Potassium Carbonate → N-Hydroxyhexyl-1,2,3,4-tetrahydroquinoline

HRID 6206

Reaction equation

HRID 6206 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[OH:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 694601,2,3,4-TetrahydroquinolineHCID 779706-Bromo-1-hexanol

Product 1

HCID 19795093N-Hydroxyhexyl-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 133.2 g (1 mole) of 1,2,3,4-tetrahydroquinoline, 181.1 g (1 mole) of 6-bromohexanol, and 138.2 g (1 mole) of potassium carbonate in toluene is heated at 80° C. for 3 hours. The solution is cooled to room temperature, and the solids are removed by filtration. The solvent is removed in vacuo, and the N-hydroxyhexyltetrahydroquinoline is purified by chromatography (silica gel, hexane:ethyl acetate).

Workup

  1. customthe solids are removed by filtration
  2. customThe solvent is removed in vacuo
  3. customthe N-hydroxyhexyltetrahydroquinoline is purified by chromatography (silica gel, hexane:ethyl acetate)

Sources & evidence

ORD record
ord-002d9f5f7d094a87a267a18d90638473
Source dataset
uspto-grants-1993_09
Patent number
US05247042

Linked notes

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