Triethylamine → 4-Methanesulphonamido-1-(4-phenyl-4-oxobutyl)piperidine

HRID 258713Notes

Reaction equation

HRID 258713 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH3:26][S:27]([NH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:12])[CH2:4][CH2:3]1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 126085374-Amino-1-(4-phenyl-4-oxobutyl)piperidine

Product 1

HCID 214265254-Methanesulphonamido-1-(4-phenyl-4-oxobutyl)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Amino-1-(4-phenyl-4-oxobutyl)piperidine (1.23 g. 0.005 m) was suspended in a solution of dichloromethane (10 mls) containing triethylamine (2 mls). Methanesulphonyl chloride (0.570 g, 0.005 m) in dichloromethane (5 mls) was added dropwise over 5 minutes and the reaction stirred overnight at room temperature. The solution was then washed with five aliquots of water and dried over magnesium sulphate. Evaporation yielded the free base in 90% purity. This was triturated in ethyl acetate and warmed. The mother liquor was decanted off and evaporated to yield the title compound m.pt 141.4° C. This was recrystallised from ethanolic HCl as the hydrochloride salt (0.510 g), m.pt 167.4° C.

Workup

  1. washThe solution was then washed with five aliquots of water
  2. dry with materialdried over magnesium sulphate
  3. customEvaporation
  4. customyielded the free base in 90% purity
  5. customThis was triturated in ethyl acetate
  6. temperaturewarmed
  7. customThe mother liquor was decanted off
  8. customevaporated

Sources & evidence

ORD record
ord-516f769c74dc4c6db94b5b6c9bfb32dc
Source dataset
uspto-grants-1977_07
Patent number
US04034098

Reaction notes

Loading…