Triethylamine → HCID 18076197, compound

HRID 901949Notes

Reaction equation

HRID 901949 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.[C:11]([C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](Cl)=[O:17])#[N:12].C(N(CC)CC)C>ClCCl>[C:11]([C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)=[O:17])#[N:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 694601,2,3,4-TetrahydroquinolineHCID 3084833-Cyanobenzoyl chloride

Product 1

HCID 18076197HCID 18076197, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,2,3,4-tetrahydroquinoline (4.2 g, 31 mmol) was added dropwise to a solution of 3-cyanobenzoyl chloride (5.2 g, 31 mmol) and triethylamine (3.1 g, 31 mmol) in dichloromethane (125 ml) while cooling in an ice/water bath. The mixture was allowed to warm to RT and stirred for 18 h. It was washed with 0.3M potassium hydrogen sulphate solution, saturated sodium hydrogen carbonate solution and brine. The organic phase was filtered through phase separation paper and reduced to yield 1-(3-cyanobenzoyl)-1,2,3,4-tetrahydroquinoline (7.1 g, 86%).

Workup

  1. temperaturewhile cooling in an ice/water bath
  2. washIt was washed with 0.3M potassium hydrogen sulphate solution, saturated sodium hydrogen carbonate solution and brine
  3. filtrationThe organic phase was filtered through phase separation paper

Sources & evidence

ORD record
ord-48451030296e458e9e4fdc676d361efd
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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