Acetic Anhydride → N-Acetoxyhexyl-1,2,3,4-tetrahydroquinoline

HRID 6207Notes

Reaction equation

HRID 6207 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:17]2[CH:12]([CH2:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1.[C:18](OC(=O)C)(=[O:20])[CH3:19].C(N(CC)CC)C>ClCCl>[C:18]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67859558N-hydroxyhexyltetrahydroquinoline

Product 1

HCID 53737711N-Acetoxyhexyl-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 233.4 g (1 mole) of N-hydroxyhexyltetrahydroquinoline and 153.1 g (1.5 moles) of acetic anhydride in dichloromethane are added 151.8 g (1.5 moles) of triethylamine and 8.5 g (1 mole %) of 4-N,N-dimethylaminopyridine, and the reaction is stirred at room temperature for 3 hours. The product solution is washed with cold 2N HCl followed by saturated sodium bicarbonate, and the organic layer is filtered through cotton and evaporated.

Workup

  1. washThe product solution is washed with cold 2N HCl
  2. filtrationthe organic layer is filtered through cotton
  3. customevaporated

Sources & evidence

ORD record
ord-bf199b56f7eb4319ac3c695eb26223f8
Source dataset
uspto-grants-1993_09
Patent number
US05247042

Reaction notes

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