4-Toluenesulfonyl chloride → 1-(2-Chloroethyl)piperidine

HRID 377421

Reaction equation

HRID 377421 reaction equation
C1(C)C=CC(S([Cl:10])(=O)=O)=CC=1.[N:12]1([CH:18](O)[CH3:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C(Cl)Cl>[Cl:10][CH2:19][CH2:18][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 30305411-(Piperidin-1-yl)ethanol

Product 1

HCID 748271-(2-Chloroethyl)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a 50 mL round bottom flask is placed 6.40 g (33.6 mmol) of p-toluenesulfonyl chloride and 25 mL of methylene chloride. The resulting solution is cooled with an ice bath as 4.00 g (31.0 mmol) of 1-piperidinoethanol in 6 mL of methylene chloride is added dropwise. After the addition is complete, the ice bath is removed and the resulting slurry is stirred for about 12 hours. The reaction mixture is concentrated on a rotary evaporator to yield a solid residue which may then be used as in Preparation 4 below.

Workup

  1. customInto a 50 mL round bottom flask is placed
  2. additionis added dropwise
  3. additionAfter the addition
  4. customthe ice bath is removed
  5. concentrationThe reaction mixture is concentrated on a rotary evaporator
  6. customto yield a solid residue which
  7. custommay then be used as in Preparation 4 below

Sources & evidence

ORD record
ord-272121b4d9e74189a3251e5a42e2b264
Source dataset
uspto-grants-2000_02
Patent number
US06025495

Linked notes

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