Methanol → HCID 58495446, compound

HRID 1191128Notes

Reaction equation

HRID 1191128 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]([CH2:27][N:28]([CH:30]([CH3:32])[CH3:31])[CH3:29])=[CH:23][CH:22]=1.CO>[NH4+].[OH-]>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[C:3]=1[NH:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:27][N:28]([CH:30]([CH3:32])[CH3:31])[CH3:29])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 86624171HCID 86624171, compound

Product 1

HCID 58495446HCID 58495446, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

Dissolve 7-chloro-6-{4-[(N-methyl-iso-propylamino)-methyl]-benzylamino}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (350 mg, 0.75 mmol) in concentrated NH4OH. (10 mL) and MeOH (10 mL). Stir the reaction mixture overnight. Concentrate the mixture in vacuo. Purify by chromatography on silica gel (45 g) eluting with a gradient of 100% DCM to 1:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) to obtain 7-chloro-6-{4-[(N-methyl-iso-propylamino)-methyl]-benzylamino}-2,3,4,5-tetrahydro-1H-benzo[d]azepine (260 mg, 93%). MS (APCI+) m/z: 372 (M+11)+.

Workup

  1. concentrationConcentrate the mixture in vacuo
  2. customPurify by chromatography on silica gel (45 g)
  3. washeluting with a gradient of 100% DCM to 1:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2)

Sources & evidence

ORD record
ord-c4f8c5d21c4e45d78d3ec9eaca2eb330
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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