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

HRID 469291Notes

Reaction equation

C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[CH2:22][CH2:23][NH:24][CH:25]1[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:27][CH2:26]1>CN(C=O)C>[CH2:31]([N:28]1[CH2:29][CH2:30][CH:25]([N:24]2[CH2:23][CH2:22][C:15]3[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=3[NH:13][C:6]2=[O:7])[CH2:26][CH2:27]1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

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 of ice water and stirred overnight. The precipitated product was suction filtered, washed with 100 mL water and dried at 45° C. in the CAD. The residue was stirred with 150 mL DIPE and suction filtered. The solid product was washed with 50 mL DIPE. After drying in the CAD at 35° C., 21.6 g of the desired product were obtained.

Workup

stirringstirred overnight
filtrationfiltered
washwashed with 100 mL water
customdried at 45° C. in the CAD
stirringThe residue was stirred with 150 mL DIPE and suction
filtrationfiltered
washThe solid product was washed with 50 mL DIPE
customAfter drying in the CAD at 35° C.

Sources & evidence

ORD record: ord-a45f6f3e0ae841aa8df17d3f88b4647e
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629137B2

Reaction notes

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