2-Bromo-1-(4-fluorophenyl)ethan-1-one → N-(4-fluorobenzoylmethyl)-2,2-dimethyl-1,2,3,4-tetrahydroquinoline

HRID 373581Notes

Reaction equation

HRID 373581 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)=[O:16]>CN(C)C=O>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]([CH2:14][N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:10][CH2:11][C:2]2([CH3:12])[CH3:1])=[O:16])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 134958062,2-Dimethyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 19810696N-(4-fluorobenzoylmethyl)-2,2-dimethyl-1,2,3,4-tetrahydroquinolineYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 2,2-dimethyl-1,2,3,4-tetrahydroquinoline (4.69 g) and 2-bromo-4'-fluoroacetophenone (3.17 g) in dry N,N-dimethylformamide (6 ml) was heated at 70°-80° C. for 5 hours under nitrogen. The reaction mixture was poured was triturated with diethyl ether to give pale yellow crystals. The crystals were collected and washed with methanol to give N-(4-fluorobenzoylmethyl)-2,2-dimethyl-1,2,3,4-tetrahydroquinoline (3.7 g).

Workup

  1. temperaturewas heated at 70°-80° C. for 5 hours under nitrogen
  2. additionThe reaction mixture was poured
  3. customwas triturated with diethyl ether
  4. customto give pale yellow crystals
  5. customThe crystals were collected
  6. washwashed with methanol

Sources & evidence

ORD record
ord-ec87b701324f4fecb7f2ebe054e1a1cb
Source dataset
uspto-grants-1992_11
Patent number
US05164400

Reaction notes

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