4-Chlorobenzylamine → HCID 86629607, compound

HRID 911359Notes

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:35]=[CH:34][C:31]([CH2:32][NH2:33])=[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:33][CH2:32][C:31]1[CH:34]=[CH:35][C:28]([Cl:27])=[CH:29][CH:30]=1

Participants

Reactant 2

HCID 660364-Chlorobenzylamine

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

Product 1

HCID 86629607HCID 86629607, compoundYield 69%

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 (700 mg, 1.6 mmol) with 4-chlorobenzylamine (354 mg, 2.5 mmol). Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 9:1) and then SCX chromatography to give 7-chloro-6-(4-chlorobenzylamino)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (459 mg, 69%). MS (ES+) m/z: 417 (M+H)+.

Workup

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

Sources & evidence

ORD record: ord-6d1c25fa376b484f87da8f9743fe79d7
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022062B2

Reaction notes

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