Piperidin-4-ol → Hpr 611

HRID 66310Notes

Reaction equation

HRID 66310 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Na].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[S:17][C:16](=[O:18])[N:15]([CH2:19][C:20](OC)=[O:21])[C:14]=2[CH:24]=1>C[O-].[Na+].CO>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:20]([CH2:19][N:15]2[C:14]3[CH:24]=[C:10]([Cl:9])[CH:11]=[CH:12][C:13]=3[S:17][C:16]2=[O:18])=[O:21])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 79341Piperidin-4-olHCID 5360545SodiumHCID 13040939Methyl 2-oxo-5-chloro-3-benzothiazolineacetate

Product 1

HCID 3082453Hpr 611Yield 80.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

4-Hydroxypiperidine (47.2 g) was added at room temperature to and dissolved in a methanolic sodium methoxide solution prepared from sodium metal (2.2 g) in dry methanol (100 ml). To the resultant solution was added methyl 5-chloro-2-oxo-3-benzothiazolineacetate (100 g), and the mixture was heated for 3 hours under reflux with stirring. The reaction mixture was left to cool, poured into ice water (500 ml) and stirred for 30 minutes. The precipitates were collected, washed with water and then dried to give 3-(4-hydroxypiperidino)carbonylmethyl-5-chloro-2-benzothiazolinone (102.5 g), which was recrystallized from 90% aqueous methanol to give colorless crystals, m.p. 180.1° C.

Workup

  1. temperaturethe mixture was heated for 3 hours
  2. temperatureunder reflux
  3. waitThe reaction mixture was left
  4. temperatureto cool
  5. stirringstirred for 30 minutes
  6. customThe precipitates were collected
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-96b26f98857542468026d27821d2f913
Source dataset
uspto-grants-1978_12
Patent number
US04131681

Reaction notes

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