Chloroacetyl chloride → 2-Chloro-N-[4-[(1-cyclobutyl-4-piperidinyl)oxy]phenyl]acetamide

HRID 1523403Notes

Reaction equation

C(N(CC)CC)C.[CH:8]1([N:12]2[CH2:17][CH2:16][CH:15]([O:18][C:19]3[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)[CH2:11][CH2:10][CH2:9]1.[Cl:26][CH2:27][C:28](Cl)=[O:29]>ClCCl>[Cl:26][CH2:27][C:28]([NH:23][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH:15]2[CH2:16][CH2:17][N:12]([CH:8]3[CH2:11][CH2:10][CH2:9]3)[CH2:13][CH2:14]2)=[CH:25][CH:24]=1)=[O:29]

Participants

Conditions

Temperature: 0 °C

Procedure

Triethylamine (66.5 g, 0.658 moles) was added to a solution of 4-[(1-Cyclobutyl-4-piperidinyl)oxy]aniline (81 g, 0.329 moles, obtained in preparation 1) in dichloromethane (1 L), at 0° C. under nitrogen atmosphere. Then the resulting mass was treated with a solution of chloro acetyl chloride (44.6 g, 0.395 moles) in dichloromethane (1 L) drop wise at 0° C. and stirred at 0° C. for 1 hour. The reaction mixture was washed with water, dried over sodium sulfate and concentrated under vacuum and the crude compound thus obtained was purified by flash chromatography (methanol:chloroform, 2:8) to obtain the title compound 76.1 g (Yield: 72%).

Workup

washThe reaction mixture was washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum
customthe crude compound thus obtained
customwas purified by flash chromatography (methanol:chloroform, 2:8)

Sources & evidence

ORD record: ord-d1f7ce2248a245a6b3342539e22c8202
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079888B2

Reaction notes

Loading…