Thionyl Chloride → tert-butyl 6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxylate

HRID 1505719Notes

Reaction equation

HRID 1505719 reaction equation
S(Cl)(Cl)=O.O[C:6]1([C:34]([F:37])([F:36])[F:35])[CH:14]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[C:12]2[CH2:23][NH:24][CH:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][N:10]3[C:11]2=[C:7]1[CH:8]=[CH:9]3>N1C=CC=CC=1>[CH2:15]([C:14]1[C:6]([C:34]([F:37])([F:36])[F:35])=[C:7]2[C:11]3=[C:12]([CH2:23][NH:24][CH:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][N:10]3[CH:9]=[CH:8]2)[CH:13]=1)[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86691987tert-butyl 7-hydroxy-6-phenethyl-7-(trifluoromethyl)-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxylate

Product 1

HCID 86691986tert-butyl 6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxylateYield 54.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Thionyl chloride (0.7 g; 5.8 mmol) was added to a solution of tert-butyl 7-hydroxy-6-phenethyl-7-(trifluoromethyl)-3,4,6,7-tetrahydro[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxylate (2.7 g; 5.8 mmol) in pyridine (7 mL) at O° C. After 2 h at 0° C., the resulting mixture was concentrated and the residue purified by silica gel chromatography (heptane-ethyl acetate) to yield tert-butyl 6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxylate (1.4 g, 53%).

Workup

  1. concentrationthe resulting mixture was concentrated
  2. customthe residue purified by silica gel chromatography (heptane-ethyl acetate)

Sources & evidence

ORD record
ord-27bad01313bc4b4192b35bc549be95fd
Source dataset
uspto-grants-2015_12
Patent number
US09216998B2

Reaction notes

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