Water → HCID 12919832, compound

HRID 851117Notes

Reaction equation

HRID 851117 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[H-].[Na+].[CH:14]([N:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][Cl:36])[CH2:29][CH2:28]1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[ClH:36].[ClH:36].[CH:14]([N:27]1[CH2:28][CH2:29][N:30]([CH2:33][CH2:34][CH2:35][N:1]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4](=[O:5])[C:2]2=[O:3])[CH2:31][CH2:32]1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7054IsatinHCID 24758Sodium hydrideHCID 10936372Piperazine, 1-(3-chloropropyl)-4-(diphenylmethyl)-

Product 1

HCID 12919832HCID 12919832, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of isatin (1.32 g) and 50% sodium hydride (0.44 g) in N,N-dimethylformamide (13 ml) was stirred for 10 minutes at ambient temperature. To the mixture was added a solution of 4-benzhydryl-1-(3-chloropropyl)piperazine (3.04 g) in N,N-dimethylformamide (6 ml) and the mixture was stirred for 2.5 hours at 50° to 60° C. The reaction mixture was poured into water (150 ml) and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated to dryness. To the residue dissolved in ethanol (30 ml) was added 29% ethanolic hydrogen chloride (6 ml), followed by an addition of diethyl ether (20 ml). The resulting precipitate was filtered and recrystallized from a mixture of methanol and diethyl ether to give crystals of 1-[3-(4-benzhydryl-1-piperazinyl)propyl]isatin dihydrochloride (1.31 g), mp. 245° to 248° C. (dec.).

Workup

  1. stirringthe mixture was stirred for 2.5 hours at 50° to 60° C
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated to dryness
  6. dissolutionTo the residue dissolved in ethanol (30 ml)
  7. additionwas added 29% ethanolic hydrogen chloride (6 ml)
  8. additionfollowed by an addition of diethyl ether (20 ml)
  9. filtrationThe resulting precipitate was filtered
  10. customrecrystallized from a mixture of methanol and diethyl ether

Sources & evidence

ORD record
ord-b3a526943bc443d68e68f73d9af33b4d
Source dataset
uspto-grants-1983_05
Patent number
US04382934

Reaction notes

Loading…