Ethyl Acetoacetate → 1-Benzyl-4-hydrazinylpiperidine

HRID 2109279Notes

Reaction equation

HRID 2109279 reaction equation
C(OCC)(=O)CC(C)=O.[CH2:10]([N:17]1[CH2:22][CH2:21][CH:20]([NH:23][NH2:24])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH:25]1([C:28]2N(C(C)C)N=[CH:30][C:29]=2[CH:36]=[O:37])CC1.C(N1CCC(=O)CC1)C1C=CC=CC=1.CN1CCC(NN)CC1>>[CH2:10]([N:17]1[CH2:18][CH2:19][CH:20]([N:23]2[C:28]([CH3:25])=[C:29]([CH:36]=[O:37])[CH:30]=[N:24]2)[CH2:21][CH2:22]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1.[CH2:10]([N:17]1[CH2:18][CH2:19][CH:20]([NH:23][NH2:24])[CH2:21][CH2:22]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 5

HCID 8868Ethyl AcetoacetateHCID 192201-Benzyl-4-piperidoneHCID 4161921-Benzyl-4-hydrazinylpiperidineHCID 109205354-Hydrazinyl-1-methylpiperidineHCID 196201355-cyclopropyl-1-(propan-2-yl)-1H-pyrazole-4-carbaldehyde

Product 2

HCID 4161921-Benzyl-4-hydrazinylpiperidineHCID 210972251-(1-Benzyl-piperidin-4-yl)-5-methyl-1H-pyrazole-4-carbaldehyde

Procedure

1-(1-Benzyl-piperidin-4-yl)-5-methyl-1H-pyrazole-4-carbaldehyde was prepared from ethyl acetoacetate and (1-benzyl-piperidin-4-yl)-hydrazine in the same manner as 5-cyclopropyl-1-isopropyl-1H-pyrazole-4-carbaldehyde (Example 49). (1-Benzyl-piperidin-4-yl)-hydrazine was prepared from 1-benzyl-piperidin-4-one in the same manner as (1-methyl-piperidin-4-yl)-hydrazine (Example 92).

Sources & evidence

ORD record
ord-88e3dcf0948c4fbc9e8a474c3810e9fd
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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