Diethyl Ether → Piperidine, 1-(3-chloropropyl)-

HRID 2176730Notes

Reaction equation

HRID 2176730 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].C(OCC)C>O>[Cl:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 79624N-(3-chloropropyl)piperidine hydrochloride

Product 1

HCID 79625Piperidine, 1-(3-chloropropyl)-Yield 94.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(3-Chloropropyl)-piperidine hydrochloride (97% purity from Aldrich Chemicals) (100 g) was dissolved in water (150 mL) and saturated aqueous potassium carbonate (250 mL) was slowly added to it. Also, 10N sodium hydroxide (25 mL) and diethyl ether (250 mL) were added and the mixture was stirred for one hour. The layers were separated; the organic layer was dried over anhydrous potassium carbonate and concentrated on a Büchi Labortechnik AG Rotavapor® evaporator to give the title compound (77.2 g, 94.4%), which was used without purification for the next reactions.

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over anhydrous potassium carbonate
  3. concentrationconcentrated on a Büchi Labortechnik AG Rotavapor® evaporator

Sources & evidence

ORD record
ord-61e3c5fa3dda480290d1f82d31ba0045
Source dataset
uspto-grants-2015_06
Patent number
US09067875B2

Reaction notes

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