Dimethylformamide → 3-(1-Benzylpiperidin-4-yl)-7-methoxy-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

HRID 2059972Notes

Reaction equation

HRID 2059972 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][CH2:11][NH:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1.CN([CH:29]=[O:30])C>>[CH2:19]([N:16]1[CH2:17][CH2:18][CH:13]([N:12]2[CH2:11][CH2:10][C:3]3[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=3[NH:1][C:29]2=[O:30])[CH2:14][CH2:15]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 59626805[2-(2-Amino-5-methoxyphenyl)-ethyl]-(1-benzylpiperidin-4-yl)-amine

Product 1

HCID 596268033-(1-Benzylpiperidin-4-yl)-7-methoxy-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

Conditions

Temperature
100 °C

Procedure

35.0 g (216 mmol) N,N′-carbonyldiimidazole were added to 23.9 g (70.3 mmol) [2-(2-amino-5-methoxyphenyl)-ethyl]-(1-benzylpiperidin-4-yl)-amine in 175 mL DMF and the mixture was stirred for 2 h at 100° C. The reaction mixture was poured onto approx. 1 kg ice water and stirred overnight. The precipitated product was suction filtered, washed with water and dried. The residue was stirred with DIPE and suction filtered. The solid product was washed with DIPE and dried.

Workup

  1. stirringstirred overnight
  2. filtrationfiltered
  3. washwashed with water
  4. customdried
  5. stirringThe residue was stirred with DIPE and suction
  6. filtrationfiltered
  7. washThe solid product was washed with DIPE
  8. customdried

Sources & evidence

ORD record
ord-5ff897c93be940048198a9329c934de8
Source dataset
uspto-grants-2012_10
Patent number
US08278336B2

Reaction notes

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