Ethanol → (s)-1-Chloro-3-(4-methylsulfonyl-1-piperazinyl)-2-propanol

HRID 1782405Notes

Reaction equation

HRID 1782405 reaction equation
[CH2:1]([C@H:3]1[O:5][CH2:4]1)[Cl:2].[CH3:6][NH:7][SH:8](=[O:10])=[O:9].[NH:11]1[CH2:16]CN[CH2:13][CH2:12]1.[CH2:17](O)C>>[Cl:2][CH2:1][C@@H:3]([OH:5])[CH2:4][N:11]1[CH2:12][CH2:13][N:7]([S:8]([CH3:17])(=[O:10])=[O:9])[CH2:6][CH2:16]1

Participants

4

Reactant 3

HCID 702EthanolHCID 149428(+)-EpichlorohydrinHCID 178420793HCID 178420793, compound

Product 1

HCID 44249051(s)-1-Chloro-3-(4-methylsulfonyl-1-piperazinyl)-2-propanol

Procedure

(S)-Epichlorohydrin (48.0 mL, 0.612 mol) was added to a stirred solution of piperazine N-methylsulfonamide (87.3 g, 0.532 mol) in ethanol (1.33 L) at room temperature. The reaction mixture was stirred for 18 h and the white solid precipitate which formed was collected by filtration and washed with ethanol to afford (S)-1-chloro-3-(4-methylsulfonyl-1-piperazinyl)-2-propanol (107.76 g) as a white solid which was used without further purification. (m/z): [M+H]+ calcd for C8H17ClN2O3S, 257.07; found, 257.2. 1H-NMR (DMSO): δ (ppm) 2.37 (dd, 1H), 2.45 (dd, 1H), 2.50-2.58 (m, 4H), 2.86 (s, 3H), 3.09 (m, 4H), 3.55 (dd, 1H), 3.65 (dd, 1H), 3.84 (m, 1H), 5.09 (d, 1H).

Workup

  1. customthe white solid precipitate which formed
  2. filtrationwas collected by filtration
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-cc19a12757ec4654bd758bcbb9d224fb
Source dataset
uspto-grants-2009_03
Patent number
US07498442B2

Reaction notes

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