Carbonate Ion → 11-[[3-[(Diethylamino)methyl]-1-piperidinyl]acetyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Reaction equation
[CH2:1]([N:3]([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]1)[CH2:4][CH3:5])[CH3:2].Cl[CH2:14][C:15]([N:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:21](=[O:28])[NH:20][C:19]2[CH:29]=[CH:30][CH:31]=[N:32][C:18]1=2)=[O:16].C(=O)([O-])[O-]>CN(C)C=O>[CH2:1]([N:3]([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([CH2:14][C:15]([N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[C:21](=[O:28])[NH:20][C:19]3[CH:29]=[CH:30][CH:31]=[N:32][C:18]2=3)=[O:16])[CH2:8]1)[CH2:4][CH3:5])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-[(diethylamino)-methyl]piperidine (4.6 g, 0.027 mol) in dry dimethylformamide (10 ml) is added dropwise over 2 hours to a suspension of 11-chloroacetyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one (5.2 g, 0.0181 mol) in anhydrous dimethylformamide (25 ml), then the resulting mixture is stirred for a further 6 hours at ambient temperature and left to stand overnight. The mixture is stirred into ice (200 g), made alkaline with postassium carbonate and extracted exhaustively with dichloromethane. The combined dichloromethane extracts are washed once with water (20 ml), dried over magnesium sulphate and concentrated by evaporation in vacuo. After recrystallization from ethyl acetate, colorless crystals (4.5 g) are obtained, mp. 199°-200° C.
Workup
- waitleft
- waitto stand overnight
- extractionextracted exhaustively with dichloromethane
- washThe combined dichloromethane extracts are washed once with water (20 ml)
- dry with materialdried over magnesium sulphate
- concentrationconcentrated by evaporation in vacuo
- customAfter recrystallization from ethyl acetate, colorless crystals (4.5 g)
- customare obtained
Sources & evidence
- ORD record
- ord-83ad965268b6480bbafe7dcc759189d3
- Source dataset
- uspto-grants-1985_10
- Patent number
- US04550107
Reaction notes
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