Triphenylphosphine → HCID 22935213, compound

HRID 970048Notes

Reaction equation

HRID 970048 reaction equation
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][Br:12].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C>[Br-:12].[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 22935207HCID 22935207, compound

Product 1

HCID 22935213HCID 22935213, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 300 ml of acetonitrile was dissolved 14.7 g (65 mmol) of (5,6,7,8-tetrahydroquinolin-2-yl)methyl bromide, and 25.5 g (97.5 mmol) of triphenylphosphine was added to the mixture and the resulting mixture was refluxed for 2 hours. After cooling the mixture with an ice-bath, precipitates were collected by filtration and washed with diethyl ether to obtain (5,6,7,8-tetrahydroquinolin-2-yl)methyltriphenylphosphonium bromide as pale yellowish solid. Then, the obtained solid was dissolved in 250 ml of chloroform, 9.50 g (117 mmol) of 37% formaldehyde and 8.10 g (76 mmol) of an aqueous sodium carbonate solution (20 ml) were added to the solution and the mixture was stirred at room temperature for 2 hours.

Workup

  1. additionwas added to the mixture
  2. temperaturethe resulting mixture was refluxed for 2 hours
  3. temperatureAfter cooling the mixture with an ice-bath
  4. customprecipitates
  5. filtrationwere collected by filtration
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-6d61f6c7397f40919a1cda8fa5a26970
Source dataset
uspto-grants-2007_12
Patent number
US07309718B2

Reaction notes

Loading…