1,3,4,5-Tetrahydro-3-[1-(phenylmethyl)-4-piperidinyl]-2H-1,3-benzodiazepin-2-one → 3-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one
Reaction equation
C1(C[N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:20][CH2:19][C:18]4[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=4[NH:16][C:15]3=[O:25])[CH2:10][CH2:9]2)C=CC=CC=1.[H][H]>CO.[Pd]>[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH2:20][CH2:19][C:18]3[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=3[NH:16][C:15]2=[O:25])[CH2:12][CH2:13]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
10.00 kg (29.81 mol, 1.0 eq) 3-[1-(phenylmethyl)-4-piperidinyl]-2,3,4,5-tetrahydro-1,3-benzodiazepin-2(1H)-one from Example 3 are dissolved in 100 L methanol, combined with 1.00 kg 10% Pd/C and hydrogenated in the pressurised reactor at 70° C. and 3 bar. After the uptake of hydrogen has ended the catalyst is filtered off and washed with 30 L methanol. The filtrate is concentrated in vacuo and the residue is suspended in 100 L acetone. Then it is refluxed, the suspension is stirred for 15 minutes at reflux temperature and half the acetone is distilled off under normal pressure. After distillation has ended the mixture is cooled to 0° C. and stirred for a further hour. The product is suction filtered, washed with 20 L acetone and dried at 50° C.
Workup
- filtrationis filtered off
- washwashed with 30 L methanol
- concentrationThe filtrate is concentrated in vacuo
- temperatureThen it is refluxed
- temperatureat reflux temperature and half the acetone
- distillationis distilled off under normal pressure
- distillationAfter distillation
- stirringstirred for a further hour
- filtrationfiltered
- washwashed with 20 L acetone
- customdried at 50° C.
Sources & evidence
- ORD record
- ord-40d7743b17064b509b26cb852140b1a4
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07141667B2
Reaction notes
Loading…