N-(3-chloropropyl)piperidine hydrochloride → HCID 20312089, compound

HRID 2420531Notes

Reaction equation

HRID 2420531 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[NH:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:2]1.[Na].Cl.Cl[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>CN(C=O)C.C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[NH:14][C:13](=[O:15])[N:12]([CH2:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[C:11]2=[O:16])=[CH:2]1

Participants

6

Reactant 3

HCID 79624N-(3-chloropropyl)piperidine hydrochlorideHCID 5360545SodiumHCID 20186934HCID 20186934, compound

Product 1

HCID 20312089HCID 20312089, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

5-(Indol-3-yl)hydantoin (8.6 g, 0.04 mole) in 200 ml of DMF was added to a solution of sodium (1.84 g, 0.08 mole) in 150 ml of anhydrous C2H5OH. N-(3-Chloropropyl)piperidine hydrochloride (7.9 g, 0.04 mole) was added and the mixture was heated to reflux with stirring for 18 hours, filtered and concentrated in vacuo to dryness. The concentrate was crystallized from aqueous methanol and twice recrystallized from aqueous DMF, yield 1.7 g, mp 233°-4° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to dryness
  5. customThe concentrate was crystallized from aqueous methanol
  6. customtwice recrystallized from aqueous DMF, yield 1.7 g, mp 233°-4° C.

Sources & evidence

ORD record
ord-a5442f0c0a3f40baa5db9b7c939d6cec
Source dataset
uspto-grants-1978_08
Patent number
US04110536

Reaction notes

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