1,2,3,4-Tetrahydro-benzo[b]azepin-5-one Chemical Properties

Boiling point:

314.6±12.0 °C(Predicted)

Density 

1.100±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

3.05±0.20(Predicted)

form 

Powder

color 

White to light green

InChI

InChI=1S/C10H11NO/c12-10-6-3-7-11-9-5-2-1-4-8(9)10/h1-2,4-5,11H,3,6-7H2

InChIKey

NKRKBYFBKLDCFB-UHFFFAOYSA-N

SMILES

N1C2=CC=CC=C2C(=O)CCC1

CAS DataBase Reference

1127-74-8(CAS DataBase Reference)

Safety Information

HazardClass 

IRRITANT

HS Code 

2933998090

1,2,3,4-Tetrahydro-benzo[b]azepin-5-one Usage And Synthesis

Synthesis

Polyphosphoric acid (25g) was heated at 100°C under nitrogen until it could be stirred. 1-(Toluene-4-sulfonyl)-1,2,3,4-tetrahydro-benzo[b]azepin-5-one (2.6g, 8.2 6mmol) was added portion-wise and the reaction mixture was heated at 100°C for 1.5h. It was poured into ice and basified with 2M NaOH(aq). The aqueous layer was extracted twice with dichloromethane. The organic extracts were combined, washed with brine, dried and reduced in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 40percent EtOAc: 60percent hexane) to yield 1,2,3,4-Tetrahydro-benzo[b]azepin-5-one (1.05g, 79percent).

References

[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 19, p. 8670 - 8692
[2] Patent: WO2006/21213, 2006, A2. Location in patent: Page/Page column 34
[3] Patent: WO2005/37796, 2005, A1. Location in patent: Page/Page column 39
[4] Journal of Organic Chemistry, 2016, vol. 81, # 8, p. 3136 - 3148

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