Triethylamine → HCID 13064787, compound

HRID 1979769Notes

Reaction equation

HRID 1979769 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][C:14](=[O:18])[NH:15]2)=[CH:10][CH:9]=1.[CH2:19]([CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:19]([CH:26]1[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][C:14](=[O:18])[NH:15]3)=[CH:10][CH:9]=2)[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 317384-BenzylpiperidineHCID 516892Sodium BicarbonateHCID 14289478HCID 14289478, compound

Product 1

HCID 13064787HCID 13064787, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.7 Grams of 7-(5-bromopentoxy)-3,4-dihydrocarbostyril, 2.0 g of 4-benzylpiperidine and 1.5 g of triethylamine were mixed with 30 ml of dimethylformamide and the mixture was heated at 60°-70° C. for 6 hours. The reaction mixture was then concentrated under a reduced pressure to dryness, and to the residue thus obtained was added a 5%-sodium hydrogencarbonate aqueous solution and stirred. The insoluble matters thus formed were collected by filtration, washed with water and dried. Recrystallization from ligroin to obtain 3.6 g (yield: 88%) of 7-[5-(4-benzyl-1-piperidyl)pentoxy]-3,4-dihydrocarbostyril as in the form of colorless plate-like crystals. Melting point: 100°-102° C.

Workup

  1. temperaturethe mixture was heated at 60°-70° C. for 6 hours
  2. concentrationThe reaction mixture was then concentrated under a reduced pressure to dryness
  3. customto the residue thus obtained
  4. customThe insoluble matters thus formed
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried
  8. customRecrystallization from ligroin

Sources & evidence

ORD record
ord-d4abbff3104442bfb2666db86f5fc95a
Source dataset
uspto-grants-1984_11
Patent number
US04482560

Reaction notes

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