1-(4-Chlorophenyl)ethylamine → HCID 86629627, compound

HRID 911386Notes

Reaction equation

HRID 911386 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.[Cl:27][C:28]1[CH:36]=[CH:35][C:31]([CH:32]([NH2:34])[CH3:33])=[CH:30][CH:29]=1>>[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]=1[NH:34][CH:32]([C:31]1[CH:35]=[CH:36][C:28]([Cl:27])=[CH:29][CH:30]=1)[CH3:33]

Participants

3

Reactant 2

HCID 978031-(4-Chlorophenyl)ethylamineHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 86629627HCID 86629627, compoundYield 38%

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 (852 mg, 2.0 mmol) and (±)-4-chloro-(α-methyl)benzylamine (622 mg, 4.0 mmol). Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 9:1) to obtain (±)-7-chloro-6-[1-(4-chlorophenyl)-ethylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (326 mg, 38%). MS (ES+) m/z: 431 (M+H)+.

Workup

  1. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 9:1)

Sources & evidence

ORD record
ord-4c33f7e7a1864b078e74db514d63c8e7
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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