Methanesulfonyl chloride → HCID 21278904, compound

HRID 2291566Notes

Reaction equation

HRID 2291566 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([CH3:17])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>N1C=CC=CC=1>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:19]([CH3:18])(=[O:21])=[O:20])=[C:12]([CH3:17])[CH:11]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 212789121-[4-(4-Amino-3-methylphenyl)piperazin-1-yl]ethan-1-one

Product 1

HCID 21278904HCID 21278904, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Acetyl-4-(4-amino-3-methylphenyl)piperazine (7.89 g) was dissolved in pyridine (130 ml). Methanesulphonyl chloride (7.9 ml) was added dropwise with stirring. The mixture was reduced in volume after 2 hours by evaporation and then stirred overnight. The resulting slurry was partitioned between water (125 ml) and dichloromethane (100 ml), and the aqueous layer was further extracted with dichloromethane (2×100 ml), 5% methanol in dichloromethane (2×100 ml), and ethyl acetate (2×125 ml). The combined organic layers were dried (sodium sulphate) and evaporated, and the residue was chromatographed in 5% methanol in dichloromethane over t.l.c. grade silica, the product-containing fractions, after evaporation, yielding a foam (5.93 g), Rf 0.29 (5% methanol/dichloromethane/silica), used directly in step (D). A small sample from a second run was recrystallized from ethyl acetate/hexane, m.p. 153°-4°.

Workup

  1. customThe mixture was reduced in volume after 2 hours by evaporation
  2. stirringstirred overnight
  3. customThe resulting slurry was partitioned between water (125 ml) and dichloromethane (100 ml)
  4. extractionthe aqueous layer was further extracted with dichloromethane (2×100 ml), 5% methanol in dichloromethane (2×100 ml), and ethyl acetate (2×125 ml)
  5. dry with materialThe combined organic layers were dried (sodium sulphate)
  6. customevaporated
  7. customthe residue was chromatographed in 5% methanol in dichloromethane over t.l.c
  8. customgrade silica, the product-containing fractions, after evaporation

Sources & evidence

ORD record
ord-733c95189d184b8bb461a72b04062d3e
Source dataset
uspto-grants-1989_01
Patent number
US04797401

Reaction notes

Loading…