Lithium hydroxide, monohydrate → HCID 59828862, compound
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][NH:28][C:29]([CH:31]2[CH2:33][CH2:32]2)=[O:30])=[CH:23][CH:22]=1.O[Li].O>CO>[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][NH:28][C:29]([CH:31]2[CH2:32][CH2:33]2)=[O:30])=[CH:25][CH:26]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Dissolve 7-chloro-6-{4-[(cyclopropanecarbonyl-amino)-methyl]-benzylamino}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (335 mg, 0.698 mmol) in MeOH (10 mL). Add LiOH.H2O (293 mg, 6.98 mmol) and stir overnight. Partition the reaction mixture between chloroform and water. Separate the aqueous phase and extract three times with chloroform and once with chloroform/iso-propanol (3:1). Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel (40 g, pre-packed cartridge) eluting with DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) (1:0 over 5 min, 19:1 over 5 min, 9:1 over 5 min, 85:15; 50 mL/min) to obtain 7-chloro-6-{-4-[(cyclopropanecarbonyl-amino)-methyl]-benzylamino}-2,3,4,5-tetrahydro-1H-benzo[d]azepine (244 mg, 91%). MS (APCI+) m/z: 384 (M+H)+.