Dimethylformamide → 5-(Indol-3-ylmethyl)-3-[3-(4-phenyl-1-piperidyl)propyl]hydantoin

HRID 2420532

Reaction equation

HRID 2420532 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]2[NH:15][C:14](=[O:16])[NH:13][C:12]2=[O:17])=[CH:2]1.Cl[CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:24][CH2:23]1.CN(C=O)C.CC[O-].[Na+]>C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]2[NH:15][C:14](=[O:16])[N:13]([CH2:19][CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][CH:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:26][CH2:27]3)[C:12]2=[O:17])=[CH:2]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 2036891-(3-Chloropropyl)-4-phenylpiperidineHCID 2428675-(1h-Indol-3-ylmethyl)imidazolidine-2,4-dioneHCID 2723922Sodium ethoxide

Product 1

HCID 203120885-(Indol-3-ylmethyl)-3-[3-(4-phenyl-1-piperidyl)propyl]hydantoin

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(indol-3-ylmethyl)hydantoin (6.4 g, 0.028 mole), 1-(3-chloropropyl)-4-phenylpiperidine (6.6 g, 0.028 mole) and 200 ml of DMF in 200 ml of anhydrous C2H5OH and 0.028 mole of NaOC2H5 was heated under reflux with stirring for 10 hours. The mixture was filtered and the filtrate was diluted with H2O. The solid was collected and twice recrystallized from aqueous C2H5OH, yield 2.0 g, mp 179°-80°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. filtrationThe mixture was filtered
  4. additionthe filtrate was diluted with H2O
  5. customThe solid was collected
  6. customtwice recrystallized from aqueous C2H5OH, yield 2.0 g, mp 179°-80°

Sources & evidence

ORD record
ord-2790ea9f42f44c8e8957db5bb79757ec
Source dataset
uspto-grants-1978_08
Patent number
US04110536

Linked notes

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