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

HRID 74495Notes

Reaction equation

HRID 74495 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 100 mL water and dried. The residue was stirred with 150 mL DIPE and suction filtered. The solid product was washed with 50 mL DIPE and dried.

Workup

  1. stirringstirred overnight
  2. filtrationfiltered
  3. washwashed with 100 mL water
  4. customdried
  5. stirringThe residue was stirred with 150 mL DIPE and suction
  6. filtrationfiltered
  7. washThe solid product was washed with 50 mL DIPE
  8. customdried

Sources & evidence

ORD record
ord-4b696820694d4e6da4478bd52c6c6adb
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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