Methanol → 6-(4-carboxy-benzylamino)-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 911372

Reaction equation

HRID 911372 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8](C(=O)C(F)(F)F)[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([O:29]C)=[O:28])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].CO>O>[C:27]([C:24]1[CH:23]=[CH:22][C:21]([CH2:20][NH:19][C:3]2[C:4]3[CH2:10][CH2:9][NH:8][CH2:7][CH2:6][C:5]=3[CH:17]=[CH:18][C:2]=2[Cl:1])=[CH:26][CH:25]=1)([OH:29])=[O:28]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 576561767-chloro-6-(4-methoxycarbonyl-benzylamino)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 576564546-(4-carboxy-benzylamino)-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 7-chloro-6-(4-methoxycarbonyl-benzylamino)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (70 mg, 0.16 mmol), potassium carbonate (0.87 g, 6.3 mmol), methanol (2 mL), water (2 mL) and heat at 50° C. for 3 h. Purify by SCX chromatography to obtain 6-(4-carboxy-benzylamino)-7-chloro-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil.

Workup

  1. customPurify by SCX chromatography

Sources & evidence

ORD record
ord-0cbddcfa307e4d6983dc4a03148831c0
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Linked notes

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