1-Bromodecane → 1-Decyl-1,2,3,4-tetrahydro-8-quinolinol

HRID 1905392Notes

Reaction equation

HRID 1905392 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH2:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>CN(C)P(=O)(N(C)C)N(C)C.CCOCC>[CH2:18]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH2:4][CH2:3][CH2:2]1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 3

HCID 81731-BromodecaneHCID 2414901,2,3,4-Tetrahydroquinolin-8-olHCID 516892Sodium Bicarbonate

Product 1

HCID 156313281-Decyl-1,2,3,4-tetrahydro-8-quinolinolYield 107.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of 499.2 mg (3.35 mmol) of 1,2,3,4-tetrahydro-8-quinolinol (see Example 7A), 425 mg (5.05 mmol, 1.5 eq.) of sodium bicarbonate, and 780 μl (3.69 mmol, 1.1 eq.) of 98% 1-bromodecane in 10 ml of hexamethylphosphoric triamide under argon was stirred for three hours at room temperature, followed by 44 hours at 50° C. The reaction was diluted with 80 ml of 1:1 ether:petroleum ether and the organic layer was washed with five 40 ml portions of water and 40 ml of brine, dried over sodium sulfate and evaporated to yield 1.04 g of a brown oil. Purification by flash chromatography on 110 g of silica, eluted with 5:95 ethyl acetate:petroleum ether afforded 624.4 mg of the title compound as a colorless oil.

Workup

  1. waitfollowed by 44 hours at 50° C
  2. washpetroleum ether and the organic layer was washed with five 40 ml portions of water and 40 ml of brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-870682707a0445e094610d22990f1c95
Source dataset
uspto-grants-1989_06
Patent number
US04843082

Reaction notes

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