Triethylamine → HCID 13064794, compound

HRID 1979777Notes

Reaction equation

HRID 1979777 reaction equation
[CH3:1][N:2]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH2:14][CH2:15]Br)=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:3]1=[O:4].[C:17]([C:20]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)(=[O:19])[CH3:18].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:1][N:2]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH2:14][CH2:15][N:23]3[CH2:24][CH2:25][C:20]([C:17](=[O:19])[CH3:18])([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:21][CH2:22]3)=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:3]1=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1015214-Acetyl-4-phenylpiperidineHCID 516892Sodium BicarbonateHCID 20438625HCID 20438625, compound

Product 1

HCID 13064794HCID 13064794, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.43 Grams of 1-methyl-6-(2-bromoethoxy)-3,4-dihydrocarbostyril, 1.3 g of 4-acetyl-4-phenylpiperidine and 1 g of triethylamine were mixed with 30 ml of dimethylformamide and the mixture was heated at 60°-70° C. for 5 hours. The reaction mixture thus obtained was concentrated under a reduced pressure to dryness, and to the residue thus obtained was added 5% sodium hydrogencarbonate aqueous solution and stirred. The insoluble matters were collected by filtration, washed with water then dried and recrystallized from ethanol-water to obtain 1.3 g of 1-methyl-6-[2-(4-acetyl-4-phenyl-1-piperidyl)ethoxy]-3,4-dihydrocarbostyril as in the form of colorless prism-like crystals. Melting point: 101°-103° C.

Workup

  1. temperaturethe mixture was heated at 60°-70° C. for 5 hours
  2. customThe reaction mixture thus obtained
  3. concentrationwas concentrated under a reduced pressure to dryness
  4. customto the residue thus obtained
  5. filtrationThe insoluble matters were collected by filtration
  6. washwashed with water
  7. customthen dried
  8. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-58cb33535bce4f38bab9772d1e46569c
Source dataset
uspto-grants-1984_11
Patent number
US04482560

Reaction notes

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