Sodium hydride → HCID 58117917, compound

HRID 405935Notes

Reaction equation

[CH2:1]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@@H:9]1[CH2:14][NH:13][C:12](=[O:15])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1>CN(C)C=O>[CH2:16]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@@H:9]1[CH2:14][N:13]([CH2:30][C:29]2[CH:32]=[CH:33][C:26]([F:25])=[CH:27][CH:28]=2)[C:12](=[O:15])[CH2:11][CH2:10]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 70 °C

Procedure

0.8 g (S)-5-dibenzylaminopiperidin-2-one (see 5.1) are placed in 8 ml dimethylformamide, then 200 mg sodium hydride (60% in mineral oil) and 0.4 ml 4-fluorobenzylbromide are added. The reaction mixture is stirred overnight at 70° C. and then combined with ice water. The precipitate is filtered off and washed with water. The product is purified by chromatography (silica gel, petroleum ether/ethyl acetate and ethyl acetate/methanol). 0.5 g product are obtained as an oil. Analytical HPLC-MS (method A): RT=1.21 min.

Workup

filtrationThe precipitate is filtered off
washwashed with water
customThe product is purified by chromatography (silica gel, petroleum ether/ethyl acetate and ethyl acetate/methanol)

Sources & evidence

ORD record: ord-f8d79e01c67a407a9c405e6ef2390a00
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754073B2

Reaction notes

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