Methyl Isocyanate → 1-(N-methylcarbamoyl)-3-phthalimidopiperidine

HRID 1415567Notes

Reaction equation

HRID 1415567 reaction equation
[C:1]1(=[O:17])[N:5]([CH:6]2[CH2:11][CH2:10][CH2:9][NH:8][CH2:7]2)[C:4](=[O:12])[C:3]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:2]12.[CH3:18][N:19]=[C:20]=[O:21]>C1C=CC=CC=1>[CH3:18][NH:19][C:20]([N:8]1[CH2:9][CH2:10][CH2:11][CH:6]([N:5]2[C:4](=[O:12])[C:3]3=[CH:13][CH:14]=[CH:15][CH:16]=[C:2]3[C:1]2=[O:17])[CH2:7]1)=[O:21]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 199722632-(Piperidin-3-yl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 214828721-(N-methylcarbamoyl)-3-phthalimidopiperidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 11.5 g. of 3-phthalimidopiperidine and 2.85 g. of methyl isocyanate in 100 ml. of dry benzene is stirred at 25° C. for 2 hours. The resulting mixture is concentrated in vacuo and filtered to give 1-(N-methylcarbamoyl)-3 -phthalimidopiperidine. Treating this phthalimidopiperidine with hydrazine hydrate by the procedure of Example 17 gives 1-(N-methylcarbamoyl)-3-aminopiperidine.

Workup

  1. additionA mixture of 11.5 g
  2. concentrationThe resulting mixture is concentrated in vacuo
  3. filtrationfiltered

Sources & evidence

ORD record
ord-c7f55a5ee22f4b9682a3af218dd63c7c
Source dataset
uspto-grants-1977_01
Patent number
US04005208

Reaction notes

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