1-(Thiophen-3-yl)ethan-1-amine → HCID 86629642, compound

HRID 911404Notes

Reaction equation

HRID 911404 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.[S:27]1[CH:31]=[CH:30][C:29]([CH:32]([NH2:34])[CH3:33])=[CH:28]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:14])([F:13])[F:15])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:34][CH:32]([C:29]1[CH:30]=[CH:31][S:27][CH:28]=1)[CH3:33]

Participants

3

Reactant 2

HCID 142499151-(Thiophen-3-yl)ethan-1-amineHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 86629642HCID 86629642, compoundYield 53%

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 (200 mg, 0.47 mmol) with (±)-1-thiophen-3-yl-ethylamine (prepared as described in J. Heterocycl. Chem. 1988, 25, 1571-1581) (90 mg, 0.70 mmol). Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1 and 4:1) to give (±)-7-chloro-6-(1-thiophen-3-yl-ethylamino)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (100 mg, 53%).

Workup

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

Sources & evidence

ORD record
ord-c39ce7ceb7864020abb3157e88a39d39
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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