Thionyl Chloride → 1-Diphenylmethyl-4-chloromethylpiperidine

HRID 362886Notes

Reaction equation

HRID 362886 reaction equation
O=S(Cl)[Cl:3].[C:5]1([CH:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:12]2[CH2:17][CH2:16][CH:15]([CH2:18]O)[CH2:14][CH2:13]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C1C=CC=CC=1>[C:5]1([CH:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][Cl:3])[CH2:14][CH2:13]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21993744(1-Benzhydrylpiperidin-4-yl)methanol

Product 1

HCID 538573511-Diphenylmethyl-4-chloromethylpiperidineYield 70.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Step 2): SOCl2 (0.6 ml, 8.2 mmol) was added dropwise to a solution of 1-diphenylmethyl-4-hydroxymethylpiperidine (1.0 g, 3.6 mmol) in benzene (7 ml) at room temperature. The mixture was refluxed for 18 hours and then concentrated. The residue was dissolved in ethyl acetate, washed with 5% NaOH solution, dried (MgSO4) and concentrated. The residue was recrystallized (ethyl acetate/ether/hexane) to give 1-diphenylmethyl-4-chloromethylpiperidine (70.1%): mp 73°-75° C.

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with 5% NaOH solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was recrystallized (ethyl acetate/ether/hexane)

Sources & evidence

ORD record
ord-883bfd377000480180b1a6f8d62435ce
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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