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1,1-Dimethylhydrazine → [4-(Dimethyl-hydrazono)-piperidin-1-yl]-dimethyl-amine

HRID 44132
Notes
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Reaction equation

HRID 44132 reaction equation
[CH3:1][N:2]([CH3:10])[N:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[CH3:11][N:12]([CH3:14])[NH2:13]>>[CH3:11][N:12]([CH3:14])[N:13]=[C:6]1[CH2:7][CH2:8][N:3]([N:2]([CH3:10])[CH3:1])[CH2:4][CH2:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 59761,1-DimethylhydrazineHCID 567377821-(Dimethylamino)-4-piperidinone

Product 1

HCID 67227495[4-(Dimethyl-hydrazono)-piperidin-1-yl]-dimethyl-amineYield 93.9%

Procedure

3.0 g 1-Dimethylamino-piperidin-4-one (prepared as described in Journal of Medicinal & Pharmaceutical Chemistry, 4, 423-36; 1961) is cooled to 0° C., and 3.8 g N,N-dimethylhydrazine is added at such a rate, that the internal temperature does not exceed 15° C. The mixture is stirred at ambient temperature for 3 hours. Then the excess of N,N-dimethylhydrazine is evaporated. Thus, 3.65 g [4-(Dimethyl-hydrazono)-piperidin-1-yl]-dimethyl-amine is obtained. 1H-NMR (CDCl3): 2.80 ppm (m, 2H), 2.70 ppm (m, 4H), 2.45 ppm (s, 6H), 2.42 ppm (m, 2H), 2.40 ppm (s, 6H).

Workup

  1. customdoes not exceed 15° C
  2. custom
Then the excess of N,N-dimethylhydrazine is evaporated

Sources & evidence

ORD record
ord-7d02794213254b14860cca0a61ad4295
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08541343B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes