Acetyl chloride → HCID 15729914, compound

HRID 981995Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:25])[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.CCN(CC)CC.[C:33](Cl)([CH3:35])=[O:34]>C(Cl)Cl>[C:33]([O:25][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[N:19]=[CH:20][C:21]([F:24])=[CH:22][N:23]=2)[CH2:14][CH2:13]1)(=[O:34])[CH3:35]

Participants

Conditions

Temperature: 5 °C

Procedure

A cold (5° C.) mixture of 1-(4-fluorophenyl)-4-(4-(5-fluoro-2-pyrimidinyl)-1-piperazinyl)-1-butanol monohydrochloride1 (3.0 g, 7.8 mmol) and Et3N (2.38 mL, 17.1 mmol) in CH2Cl2 (55 mL) was treated dropwise (10 min) with AcCl (0.67 mL, 9.4 mmol). The reaction mixture was stirred at 5° C. for 0.25 h and then at 23° C. for 2 h before being diluted with CH2Cl2 (250 mL). The organic solution was washed with water (30 mL), saturated Na2CO3 solution to bring pH to 9, water (20 mL) and brine, dried (MgSO4) and concentrated in vacuo to a solid which was purified on silica gel column using a mixture of 30-40% AcOEt in CH2Cl2. The appropriate fractions were collected and concentrated in vacuo to a white solid, 2.93 g, 96%. Recrystallization from ether-hexane mixture afforded analytical sample, mp 76°-7° C.

Workup

washThe organic solution was washed with water (30 mL), saturated Na2CO3 solution
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo to a solid which
customwas purified on silica gel column
additiona mixture of 30-40% AcOEt in CH2Cl2
customThe appropriate fractions were collected
concentrationconcentrated in vacuo to a white solid, 2.93 g, 96%
customRecrystallization from ether-hexane mixture
customafforded analytical sample, mp 76°-7° C.

Sources & evidence

ORD record: ord-1fec367d4aa8481b97f530424929a9e6
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04994460

Reaction notes

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