Dimethylamine → 1-(7-Dimethylaminomethyl-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-2,2,2-trifluoroethanone
Reaction equation
[CH3:1][NH:2][CH3:3].[F:4][C:5]([F:22])([F:21])[C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([CH:19]=O)=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.C(O)(=O)C>[CH3:1][N:2]([CH2:19][C:17]1[CH:16]=[CH:15][C:12]2[CH2:13][CH2:14][N:8]([C:6](=[O:7])[C:5]([F:22])([F:4])[F:21])[CH2:9][CH2:10][C:11]=2[CH:18]=1)[CH3:3]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
11.7 mL (23.4 mmol) of a 2 M dimethylamine solution in THF were added to a solution of 4.5 g (16.59 mmol) 3-(2,2,2-trifluoro-acetyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7-carbaldehyde in 150 mL THF and the solution was adjusted to pH 5 with 1 mL glacial acetic acid. After 30 min 4.62 g (21.79 mmol) sodium triacetoxyborohydride were added and the reaction mixture was stirred overnight at RT. The reaction solution was carefully combined with saturated NaHCO3 solution, stirred for 30 min, exhaustively extracted with EtOAc, the organic phase was separated off and dried over Na2SO4. After the desiccant and solvent had been eliminated the desired product was obtained, which was further reacted without purification.
Workup
- stirringstirred for 30 min
- extractionexhaustively extracted with EtOAc
- customthe organic phase was separated off
- dry with materialdried over Na2SO4
- customwas obtained
- customwhich was further reacted without purification
Sources & evidence
- ORD record
- ord-04b167256c194d23b617a099fc2f671c
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700589B2
Reaction notes
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