Methanesulfonyl chloride → HCID 19763579, compound

HRID 248463Notes

Reaction equation

HRID 248463 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][CH:9]2[CH2:21][OH:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(Cl)(=O)=O>ClCCl.C(N(CC)CC)C>[O:22]([CH2:21][CH:9]1[N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 10827800(1,4-Dibenzylpiperazin-2-yl)methanol

Product 1

HCID 19763579HCID 19763579, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A 6 g portion of 1,4-bis(phenylmethyl)-2-piperazinemethanol was dissolved in 90 ml of dichloromethane together with 4.26 ml of triethylamine and then cooled to 0°-5° C. A 2.04 ml portion of methanesulfonyl chloride was added and the mixture was allowed to warm to room temperature over 2 hours. The mixture was washed with ice cold sodium bicarbonate solution, followed twice with ice water, dried, filtered and evaporated. The residue was dissolved in dimethylformamide and added to a solution of 2.07 g of sodium phenol and 1.02 g of 50% sodium hydride in 30 ml of dimethylformamide under argon. This mixture was stirred for 48 hours, water was added and the mixture extracted twice with ether. The extracts were combined, washed with water, dried, filtered and evaporated, giving a gum which was crystallized from methanol with refrigeration, giving 4.1 g of 3-phenoxymethyl-1,4-bis(phenylmethyl)piperazine.

Workup

  1. temperaturecooled to 0°-5° C
  2. washThe mixture was washed with ice cold sodium bicarbonate solution
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe residue was dissolved in dimethylformamide
  7. additionadded to a solution of 2.07 g of sodium phenol and 1.02 g of 50% sodium hydride in 30 ml of dimethylformamide under argon
  8. additionwater was added
  9. extractionthe mixture extracted twice with ether
  10. washwashed with water
  11. customdried
  12. filtrationfiltered
  13. customevaporated
  14. customgiving a gum which
  15. customwas crystallized from methanol with refrigeration

Sources & evidence

ORD record
ord-32fa472e599349e6be2aeebcf93c7b1b
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

Loading…