Dimethylformamide → 1-[3-(4-Hydroxymethylphenoxy)-propyl]piperidine, hydrochloride

HRID 657679Notes

Reaction equation

HRID 657679 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[NH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.CN(C)C=O>O>[ClH:1].[OH:11][CH2:10][C:9]1[CH:12]=[CH:13][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 228974964-(3-Chloropropoxy)benzyl alcohol

Product 1

HCID 1317293251-[3-(4-Hydroxymethylphenoxy)-propyl]piperidine, hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(3-chloropropoxy)benzyl alcohol (11.1 g), potassium carbonate (23.0 g), piperidine (6.57 mL) and N,N-dimethylformamide (130 mL) is heated at a temperature close to 100° C. for 5 h30, then cooled back to room temperature. Water (130 mL) is added and organics are extracted with dichloromethane. The combined extracts are pooled, dried over magnesium sulphate, purified by chromatography over silica gel (eluent: dichloromethane/methanol with trace amount of ammonia from 90/10 to 80/20) to give 5.62 g of 1-[3-(4-hydroxymethylphenoxy)-propyl]piperidine, hydrochloride as a white solid used without further purification.

Workup

  1. temperatureis heated at a temperature
  2. customclose to 100° C. for 5 h30
  3. extractionorganics are extracted with dichloromethane
  4. dry with materialdried over magnesium sulphate
  5. custompurified by chromatography over silica gel (eluent: dichloromethane/methanol with trace amount of ammonia from 90/10 to 80/20)

Sources & evidence

ORD record
ord-3b17ce652eab46e6988574cf1a8b3463
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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