Dimethylformamide → 1-benzyl-5-chloro-2,3,6,7-tetrahydro-1H-azepine-4-carbaldehyde hydrochloride

HRID 400464Notes

Reaction equation

HRID 400464 reaction equation
O=P(Cl)(Cl)[Cl:3].CN([CH:9]=[O:10])C.[ClH:11].[CH2:12]([N:19]1[CH2:25][CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[ClH:3].[CH2:12]([N:19]1[CH2:25][CH2:24][C:23]([Cl:11])=[C:22]([CH:9]=[O:10])[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 130720291-Benzylazepan-4-one hydrochloride

Product 1

HCID 189435411-benzyl-5-chloro-2,3,6,7-tetrahydro-1H-azepine-4-carbaldehyde hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

77 mL phosphoroxychloride was added to 62 mL DMF at 8-18° C. 84 mL dichlormethane was added and 50 g 1-benzyl 4-azepanone hydrochloride. The reaction was stirred over night at RT. The mixture was added to 300 mL ice water and extracted with dichlormethane. The organic layer was evaporated to give 23.3 g of the desired product. (M+H)+=287

Workup

  1. extractionextracted with dichlormethane
  2. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-6d50818a27d4421b9ef657a436f1ce91
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

Loading…