Methanol → 1-(4-Methanesulphonamidophenyl)-4-(4-methanesulphonamidophenacyl)piperazine

HRID 2291573Notes

Reaction equation

HRID 2291573 reaction equation
Cl.[CH3:2][S:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1)(=[O:5])=[O:4].[CH3:19][S:20]([NH:23][C:24]1[CH:33]=[CH:32][C:27]([C:28](=[O:31])[CH2:29]Br)=[CH:26][CH:25]=1)(=[O:22])=[O:21].C(N(CC)CC)C.CO>ClCCl>[CH3:2][S:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:18][CH2:17][N:16]([CH2:29][C:28]([C:27]3[CH:26]=[CH:25][C:24]([NH:23][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:33][CH:32]=3)=[O:31])[CH2:15][CH2:14]2)=[CH:11][CH:12]=1)(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 15592151N-(4-(2-bromoacetyl)phenyl)methanesulfonamideHCID 18759927N-[4-(piperazin-1-yl)phenyl]methanesulfonamide hydrochloride

Product 1

HCID 212789191-(4-Methanesulphonamidophenyl)-4-(4-methanesulphonamidophenacyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-Methanesulphonamidophenyl)piperazine hydrochloride (1.18 g), 4-methanesulphonamidophenacyl bromide (1.16 g), [see J. Med. Chem, 9, 88 (1966)], triethylamine (0.82 g), methanol (10 ml) and dichloromethane (10 ml) were warmed briefly to attain homogeneity, then stirred at ambient temperature for 4 hours, evaporated to dryness, the residue triturated and washed with water, and then crystallized from methanol/acetone. The yield of the title compound was 0.88 g, m.p. 222°-5° (dec.).

Workup

  1. customevaporated to dryness
  2. customthe residue triturated
  3. washwashed with water
  4. customcrystallized from methanol/acetone

Sources & evidence

ORD record
ord-e2d6cdb159b0419a8276e343ac317540
Source dataset
uspto-grants-1989_01
Patent number
US04797401

Reaction notes

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