Gramine → HCID 12392199, compound

HRID 1973402Notes

Reaction equation

HRID 1973402 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][CH:6]=1)[CH3:3].[N:14]([N:16]1[CH2:21]CNC[CH2:17]1)=[O:15]>C1(C)C=CC=CC=1>[N:14]([N:16]1[CH2:21][CH2:1][N:2]([CH2:4][C:5]2[C:9]3[C:8](=[CH:13][CH:12]=[CH:11][CH:10]=3)[NH:7][CH:6]=2)[CH2:3][CH2:17]1)=[O:15]

Participants

4

Reactant 2

HCID 6890GramineHCID 21845N-Nitrosopiperazine

Product 1

HCID 12392199HCID 12392199, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 34.8 g (0.22 mol) of gramine and 23.9 g (0.20 mol) of nitrosopiperazine in 700 ml. of toluene is refluxed while stirring under nitrogen for 48 hours. The reaction solution is then concentrated under reduced pressure until a precipitate appears and then is cooled to 0° C. and is filtered. The product is washed with cold toluene and dried to produce crystals of 3-(4-nitrosopiperazin-1-yl)methylindole. This product is recrystallized from toluene to yield pure plates, m.p. 116°-118° C. Analysis: Calculated for C13H16N4O: 63.92% C; 6.60% H; 22.93% N Found: 63.84% C; 6.64% H; 23.06% N.

Workup

  1. concentrationThe reaction solution is then concentrated under reduced pressure until a precipitate
  2. filtrationis filtered
  3. washThe product is washed with cold toluene
  4. customdried

Sources & evidence

ORD record
ord-5c6eecb845d14c77a93d1eb2333593b2
Source dataset
uspto-grants-1976_12
Patent number
US03997539

Reaction notes

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