1,1-Dichloroethane → HCID 21852744, compound

HRID 1586383Notes

Reaction equation

HRID 1586383 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3](C=O)[CH:2]=1.[C:13]1([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:25](O[BH-](OC(=O)C)OC(=O)C)(=[O:27])C.[Na+].Cl[CH:40](Cl)C>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:40][N:22]1[CH2:23][CH2:24][N:19]([C:13]2[CH:18]=[CH:17][C:16]([CH2:25][OH:27])=[CH:15][CH:14]=2)[CH2:20][CH2:21]1

Participants

5

Reactant 4

HCID 63651,1-DichloroethaneHCID 70961-PhenylpiperazineHCID 836413-QuinolinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 21852744HCID 21852744, compound

Procedure

A mixture of 3-quinoline carboxaldehyde (1 g, 6.36 mmol) and 1-phenylpiperazine (6.68 mmol), and sodium triacetoxyborohydride (2 g, 9.6 mmol) and 20 mL of dichloroethane, is stirred at room temperature for 18 hours. The resulting mixture is partitioned between chloroform and aqueous sodium bicarbonate, the organic layer is dried over sodium sulfate, and the solvents were removed under reduced pressure. The residue was recrystallized from ethyl acetate to give 1.2 g of the title compound as a white solid, mp 145-147° C.

Workup

  1. customThe resulting mixture is partitioned between chloroform and aqueous sodium bicarbonate
  2. dry with materialthe organic layer is dried over sodium sulfate
  3. customthe solvents were removed under reduced pressure
  4. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0d353b8f493c49bda44e80ca30b5eda3
Source dataset
uspto-grants-1999_08
Patent number
US05945421

Reaction notes

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