Bis-(1H-imidazol-2-YL)-methanone → 1,3,4,5-Tetrahydro-3-[1-(phenylmethyl)-4-piperidinyl]-2H-1,3-benzodiazepin-2-one

HRID 2355936Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1.[C:24](C1NC=CN=1)(C1NC=CN=1)=[O:25]>O1CCCC1>[CH2:17]([N:14]1[CH2:13][CH2:12][CH:11]([N:10]2[CH2:9][CH2:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH:1][C:24]2=[O:25])[CH2:16][CH2:15]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of [2-(2-amino-phenyl)-ethyl]-(1-benzyl-piperidin-4-yl)-amine (0.44 g, 1.42 mmol) in tetrahydrofuran (5 mL) at 0° C. was treated with carbonyl diimidazole (0.23 g, 1.42 mmol). The reaction was stirred for 30 min at 0° C. and at reflux for 1 h. After cooling to room temperature, the solvent was evaporated and the residue purified by column to afford 100 mg (21%) of the desired product. LC/MS: tR=1.29 min, 336.34 (MH)+.

Workup

temperatureat reflux for 1 h
temperatureAfter cooling to room temperature
customthe solvent was evaporated
customthe residue purified by column

Sources & evidence

ORD record: ord-9b385d28bce14ddca42025bfbe708378
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754732B2

Reaction notes

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