Hydrochloric Acid → Hydrochloric Acid

HRID 66301Notes

Reaction equation

HRID 66301 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:14])[CH2:6][CH2:5]1.C(N(CC)CC)C.[C:28]1([S:34]([Cl:37])(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl>C(Cl)Cl.C(OCC)C>[C:28]1([S:34]([NH:3][CH:4]2[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][C:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:14])[CH2:6][CH2:5]2)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[ClH:37]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 227548374-Amino-1-(4-phenyl-4-oxobutyl)piperidine dihydrochloride

Product 2

HCID 313Hydrochloric AcidHCID 536955074-Benzenesulphonamido-1-(4-phenyl-4-oxobutyl)piperidine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-amino-1-(4-phenyl-4-oxobutyl)-piperidine dihydrochloride (1.752 g. 0.005 mole) and triethylamine (2 ml.) in CH2Cl2 (10 ml.) was added dropwise a solution of benzenesulphonyl chloride (0.883 g. 0.005 mole) in CH2Cl2 (5 ml.). The mixture was stirred for 24 hours and extracted with water (3 × 10 ml.). The organic phase was separated, dried (MgSO4) and evaporated to give a crystalline residue. Treatment of this with ethanolic HCl followed by diethyl ether afforded the title compound as the monohydrochloride, buff solid (1.961 g.), m.p. 195.2° C.

Workup

  1. extractionextracted with water (3 × 10 ml.)
  2. customThe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a crystalline residue

Sources & evidence

ORD record
ord-cc2887cf88b94c80aa1545108c86a644
Source dataset
uspto-grants-1978_12
Patent number
US04131680

Reaction notes

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