Sodium Chloride → HCID 4362638, compound

HRID 1612391Notes

Reaction equation

HRID 1612391 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:17][S:18](Cl)(=[O:20])=[O:19].[Na+].[Cl-]>O.C1(C)C=CC=CC=1>[CH3:17][S:18]([O:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10]1)(=[O:20])=[O:19]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 4362638HCID 4362638, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

1-Benzyl-4-piperidinol (23.98 g), 168.66 g of toluene and 83.56 g of a 30% aqueous solution of NaOH were respectively weighed and placed in a 500-mL four-necked flask. While the mixture was stirred, the flask inside temperature was lowered to 6.7° C. Then, 31.73 g of methanesulfonyl chloride was added dropwise over 4 hours and 30 minutes at a flask inside temperature of 5 to 10° C. Water (33 mL) was added to dissolve the NaCl which had precipitated out in the aqueous phase, and the mixture was separated into the toluene phase and aqueous phase. A toluene solution of 1-benzyl-4-piperidinol methanesulfonate was thus obtained in a yield of 40.3 mole percent.

Workup

  1. customplaced in a 500-mL four-necked flask
  2. customwas lowered to 6.7° C
  3. customhad precipitated out in the aqueous phase
  4. customthe mixture was separated into the toluene phase and aqueous phase

Sources & evidence

ORD record
ord-b32dc0c715cd4ce5a35728c1483a6930
Source dataset
uspto-grants-2006_01
Patent number
US06992205B2

Reaction notes

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