(4-(Aminomethyl)phenyl)(phenyl)methanone → 6-(4-benzoyl-benzylamino)-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 2041256Notes

Reaction equation

HRID 2041256 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1OS(C(F)(F)F)(=O)=O.[NH2:27][CH2:28][C:29]1[CH:42]=[CH:41][C:32]([C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:34])=[CH:31][CH:30]=1>>[C:33]([C:32]1[CH:31]=[CH:30][C:29]([CH2:28][NH:27][C:3]2[C:4]3[CH2:10][CH2:9][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:7][CH2:6][C:5]=3[CH:17]=[CH:18][C:2]=2[Cl:1])=[CH:42][CH:41]=1)(=[O:34])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

3

Reactant 2

HCID 2760963(4-(Aminomethyl)phenyl)(phenyl)methanoneHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 576565116-(4-benzoyl-benzylamino)-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 96%

Procedure

Use a method similar to the General Procedure 5-3 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (272 mg, 0.64 mmol) with 4-(aminomethyl)benzophenone (prepared by following the procedure described in J. Biol. Chem. 1993, 268 (19), 14230) (270 mg, 1.3 mmol). Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 17:3 and 4:1) to give 6-(4-benzoyl-benzylamino)-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as an oil (300 mg, 96%).

Workup

  1. customprepared
  2. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 17:3 and 4:1)

Sources & evidence

ORD record
ord-e87778bece6e459dac10565ae10762b1
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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