Acetaldehyde → HCID 19020599, compound

HRID 1109475Notes

Reaction equation

HRID 1109475 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)=[O:7])=[C:4]([Cl:25])[CH:3]=1.[CH:26](=O)[CH3:27].Cl.[BH4-].[Na+]>CO.O>[ClH:22].[CH2:26]([NH:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)=[O:7])=[C:4]([Cl:25])[CH:3]=1)[CH3:27]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 19020596HCID 19020596, compound

Product 1

HCID 19020599HCID 19020599, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1.5 g of 1-(4-amino-2-chlorobenzoyl)-4-[2-(4-chlorophenyl)ethyl]-piperazine (see Example 7) are dissolved together with 0.26 g of acetaldehyde and 0.8 ml of 5N alcoholic hydrochloric acid in 15 ml of methanol. 0.41 g of 85% NaBH4 is added thereto and the reaction solution is stirred at room temperature for 24 hours. Water is added to the reaction solution, which is then decanted off and taken up in methylene chloride, dried and concentrated by evaporation. The oily material is chromatographed on silica gel and converted into the hydrochloride, yielding 1-[4-(N-ethylamino)-2-chlorobenzoyl]-4-[2-(4-chlorophenyl)ethyl]-piperazine hydrochloride having a melting point of 230°.

Workup

  1. customis then decanted off
  2. customdried
  3. concentrationconcentrated by evaporation
  4. customThe oily material is chromatographed on silica gel

Sources & evidence

ORD record
ord-eb3ed5fabab241cd8fd2259948f0c466
Source dataset
uspto-grants-1994_06
Patent number
US05321027

Reaction notes

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