3-Fluorobenzylamine → HCID 86629647, compound

HRID 2041294Notes

Reaction equation

[F:1][C:2]([F:29])([F:28])[C:3]([N:5]1[CH2:11][CH2:10][C:9]2[C:12](OS(C(F)(F)F)(=O)=O)=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1)=[O:4].[F:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[CH2:34][NH2:35]>>[F:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[CH2:34][NH:35][C:12]1[C:9]2[CH2:10][CH2:11][N:5]([C:3](=[O:4])[C:2]([F:1])([F:28])[F:29])[CH2:6][CH2:7][C:8]=2[CH:15]=[CH:14][C:13]=1[C:16]([F:17])([F:18])[F:19]

Participants

Reactant 2

HCID 668533-Fluorobenzylamine

HCID 574477493-(2,2,2-Trifluoroacetyl)-6-trifluoromethanesulfonyloxy-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 86629647HCID 86629647, compoundYield 53%

Procedure

Use a method similar to the General Procedure 5-1 to couple 3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (110 mg, 0.24 mmol) and 3-fluorobenzyl amine (90 μL, 0.7 mmol). Purify by chromatography on silica gel eluting with hexane/EtOAc (95:5) followed by SCX chromatography to give 6-(3-fluorobenzylamino)-3-(2,2,2-trifluoroacetyl)-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (55 mg, 53%). MS (ES+) m/z: 435 (M+H)+.

Workup

customPurify by chromatography on silica gel eluting with hexane/EtOAc (95:5)

Sources & evidence

ORD record: ord-67a875f45bbf4291917ca2a82f57c6a6
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580780B2

Reaction notes

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