Dichloromethane → HCID 19028731, compound

HRID 2256345Notes

Reaction equation

HRID 2256345 reaction equation
[C:1]1([C:7]2([CH2:17][CH:18]([N:20]3[CH2:25][CH2:24][N:23]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[CH2:22][CH2:21]3)[CH3:19])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34].C(Cl)[Cl:41]>>[ClH:41].[C:33]([N:9]1[CH2:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([CH2:17][CH:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)[CH2:22][CH2:21]2)[CH3:19])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1)(=[O:35])[CH3:34]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 19028754HCID 19028754, compound

Product 1

HCID 19028731HCID 19028731, compound

Procedure

To a solution of 4-phenyl-4-{2-[4-(p-fluorophenyl)piperazin-1-yl]propyl}-1,2,3,4-tetrahydroisoquinoline (1.2 g) in methylene chloride (30 ml) was added acetic anhydride (0.33 ml) with ice-cooling and stirring and the mixture was further stirred at room temperature for 1 hour. The reaction mixture was then concentrated to dryness and the residue was purified by silica gel column chromatography (ethyl acetate-methanol=10:1) and treated with hydrochloric acid to provide the title compound (1.2 g) as white crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred at room temperature for 1 hour
  3. concentrationThe reaction mixture was then concentrated to dryness
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate-methanol=10:1)
  5. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-c7fa53e4499f4e0180679099d293b3da
Source dataset
uspto-grants-1997_08
Patent number
US05654296

Reaction notes

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