Hydrochloric Acid → (+/-)-7-Chloro-6-(2-phenyl-pyrrolidin-1-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride

HRID 1013128Notes

Reaction equation

HRID 1013128 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8](C(=O)C(F)(F)F)[CH2:9][CH2:10][C:4]=2[C:3]=1[N:19]1[CH2:23][CH2:22][CH2:21][CH:20]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CO.Cl>C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[C:3]=1[N:19]1[CH2:23][CH2:22][CH2:21][CH:20]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 59799052(+/-)-7-Chloro-3-(2,2,2-trifluoroacetyl)-6-(2-phenyl-pyrrolidin-1-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine2×

Product 1

HCID 86622862(+/-)-7-Chloro-6-(2-phenyl-pyrrolidin-1-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochlorideYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Treat (+/−)-7-chloro-3-(2,2,2-trifluoroacetyl)-6-(2-phenyl-pyrrolidin-1-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (prepared essentially as described in Preparation 38) (80 mg, 0.19 mmol) with basic methanol in a similar fashion to the isolated enantiomers of (+/−)-7-chloro-3-(2,2,2-trifluoroacetyl)-6-(2-phenyl-pyrrolidin-1-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine. Treat the resultant residue with excess 2 N HCl in diethyl ether to give the product as a white solid (57 mg, 82%).

Workup

  1. customprepared essentially

Sources & evidence

ORD record
ord-a704d2c44c204d139397d94bb0ed9a62
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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