4-Piperidin-1-ylmethyl-benzylamine → HCID 86624169, compound

HRID 1191124Notes

Reaction equation

HRID 1191124 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.[N:27]1([CH2:33][C:34]2[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]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:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:39][CH2:38][C:37]1[CH:36]=[CH:35][C:34]([CH2:33][N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:41][CH:40]=1

Participants

3

Reactant 2

HCID 52002924-Piperidin-1-ylmethyl-benzylamineHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 86624169HCID 86624169, compoundYield 72.5%

Procedure

Use a method similar to the General Procedure)-2 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethansulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (300 mg, 0.69 mmol) and 4-(piperidin-1-ylmethyl)-benzylamine (174 mg, 0.84 mmol). Purify by chromatography on silica gel (150 g) eluting with a gradient of DCM to 4:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) to obtain 7-chloro-6-[4-(piperidin-1-ylmethyl)-benzylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as an oil (240 mg, 71%). MS (ES+) m/z: 480 (M+H)+.

Workup

  1. customPurify by chromatography on silica gel (150 g)
  2. washeluting with a gradient of DCM to 4:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2)

Sources & evidence

ORD record
ord-0067b3e6680b4381944ffc97f366f915
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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