Methylhydrazine → HCID 21275426, compound

HRID 1381950Notes

Reaction equation

HRID 1381950 reaction equation
[ClH:1].[CH3:2][N:3]1[CH2:8][CH2:7][C:6]([CH2:12][C:13]([OH:15])=O)([C:9](O)=[O:10])[CH2:5][CH2:4]1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:31][NH:32][NH2:33]>CN(C)C=O>[ClH:1].[CH3:2][N:3]1[CH2:8][CH2:7][C:6]2([C:9](=[O:10])[N:33]([NH:32][CH3:31])[C:13](=[O:15])[CH2:12]2)[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 10868DicyclohexylcarbodiimideHCID 14371797HCID 14371797, compound

Product 1

HCID 21275426HCID 21275426, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide (30 ml) was dissolved (1-methyl-4-carboxypiperidin-4-yl)acetic acid.hydrochloride (1.9g). To the solution was added dicyclohexylcarbodiimide (1.82 g), and the mixture was stirred for one hour, to which was added methylhydrazine (0.43 ml). The mixture was stirred at 60° C. for one full day. Precipitates were removed, and the solvent was evaporated off under reduced pressure. The residual oily product was subjected to a silica gel column chromatography [eluent; n-butanol:acetic acid:methanol:water=1:1:1:1 (V/V)]. To the solution containing the desired product was added 4 ml of 1N hydrochloric acid. Then, the solvent was evaporated off, and the residual solid product was recrystallized from ethanol to obtain 0.25 g of colorless solid, m.p. 235° to 260° C.

Workup

  1. stirringThe mixture was stirred at 60° C. for one full day
  2. customPrecipitates
  3. customwere removed
  4. customthe solvent was evaporated off under reduced pressure
  5. additionTo the solution containing the desired product
  6. additionwas added 4 ml of 1N hydrochloric acid
  7. customThen, the solvent was evaporated off
  8. customthe residual solid product was recrystallized from ethanol

Sources & evidence

ORD record
ord-a679ede50fc64395afd259bb9ef13812
Source dataset
uspto-grants-1989_02
Patent number
US04804665

Reaction notes

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