Dimethyl Sulfoxide → HCID 22264737, compound

HRID 1533079Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[CH:38]=[CH:37][C:15]([CH2:16][N:17]2[CH2:22][CH2:21][N:20]([C:23]([CH2:25][O:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=[O:24])[CH2:19][CH:18]2[CH2:34][CH2:35][OH:36])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[F:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][N:17]2[CH2:22][CH2:21][N:20]([C:23]([CH2:25][O:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=[O:24])[CH2:19][CH:18]2[CH2:34][CH:35]=[O:36])=[CH:37][CH:38]=1

Participants

Conditions

Temperature: -50 °C

Procedure

To a solution of oxalyl chloride (0.62 g, 5 mmol) in CH2Cl2 (20 mL) at −50° C. was added DMSO (0.85 g, 11 mmol, in solution of 5 mL of CH2Cl2) over 2 minutes. 4-(4-fluorobenzyl)-1-((4-chlorophenoxy)methyl)carbonyl-3-(2-hydroxyethyl)piperazine (1.85 g, 4.5 mmol, in solution of 5 mL of CH2Cl2) was added. The resulting mixture was stirred at −50° C. for 15 minutes, then triethylamine (2.3 g, 22 mmol) was added. After 5 minutes at −50° C., the mixture was gradually warmed to ambient temperature. At that time the mixture was diluted with CH2Cl2 and washed with water, then brine. The organic layer was then dried over MgSO4 and concentrated in vacuo to afford 1.7 g of 4-(4-fluorobenzyl)-1-((4-chlorophenoxy)methyl)carbonyl-3-((formyl)methyl)piperazine as a yellow oil; NMR (CDCl3) 9.8 (d, 1) 7.3 (m, 4), 7.0 (m, 4), 4.6 (m, 3), 3.8-3.2 (m, 7), 2.7-2.2 (m, 4) ppm.

Workup

waitAfter 5 minutes at −50° C.
temperaturethe mixture was gradually warmed to ambient temperature
washwashed with water
dry with materialThe organic layer was then dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d978c82e7a0f4ef0822b32229a0ff982
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06207665B1

Reaction notes

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