Hydrochloric Acid → 3-(1-Benzyloxycarbonyl-4-piperidyl)propyl p-toluenesulfonate

HRID 280975Notes

Reaction equation

HRID 280975 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][OH:20])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22].Cl>N1C=CC=CC=1>[C:27]1([CH3:28])[CH:29]=[CH:30][C:24]([S:21]([O:20][CH2:19][CH2:18][CH2:17][CH:14]2[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[CH2:12][CH2:13]2)(=[O:23])=[O:22])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 14989193Benzyl 4-(3-hydroxypropyl)piperidine-1-carboxylate

Product 1

HCID 136527313-(1-Benzyloxycarbonyl-4-piperidyl)propyl p-toluenesulfonateYield 57.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a chilled mixture of 3-(1-benzyloxycarbonyl-4-piperidyl)propanol (110 g) and pyridine (500 ml) is added portionwise tosyl chloride (100 g) for 2 hours with stirring. After stirring for further 1 hour, ice water (1 l) is added dropwise to the mixture. The resulting mixture is acidified by dropwise addition of concentrated hydrochloric acid at ice-bath temperature and extracted with ethyl acetate (1 l). The extract is washed successively with diluted hydrochloric acid and water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is crystallized from ethanol to give 3-(1-benzyloxycarbonyl-4-piperidyl)propyl p-toluenesulfonate (99 g) as a colorless crystals, mp 59°-60° C.

Workup

  1. stirringAfter stirring for further 1 hour
  2. extractionextracted with ethyl acetate (1 l)
  3. washThe extract is washed successively with diluted hydrochloric acid and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-572987f309a24adea55430a1ae9a1c03
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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