Hydrazine hydrate (1:1) → HCID 67420203, compound

HRID 1875712Notes

Reaction equation

HRID 1875712 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH:10]([C:15](=O)[C:16]2[CH:21]=[C:20]([Cl:22])[C:19](OCC3C=CC=CC=3)=[CH:18][C:17]=2[O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:40].[NH2:41][NH2:42]>CCO.C1COCC1.C(OC(=O)C)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2[NH:41][N:42]=[C:15]([C:16]3[CH:21]=[C:20]([Cl:22])[C:19]([O:40][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:18][C:17]=3[O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67421050HCID 67421050, compound

Product 1

HCID 67420203HCID 67420203, compoundYield 174.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-benzyl-3-(2,4-bis-benzyloxy-5-chloro-benzoyl)-piperidin-4-one (26.1 g, 48 mmol) in EtOH (150 mL) and THF (100 mL) was slowly added drop wise a solution of hydrazine hydrate (10 mL, 200 mmol, 4 eq) in EtOH (25 mL). After stirring overnight, the solution was diluted with ethylacetate and thoroughly washed with water, then with brine, dried over Na2SO4 and evaporated. The residue was chromatographed on silica gel eluting with ethylacetate to give 5-benzyl-3-(2,4-bis-benzyloxy-5-chloro-phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine (a) (22.5 g, 86% yield).

Workup

  1. washthoroughly washed with water
  2. dry with materialwith brine, dried over Na2SO4
  3. customevaporated
  4. customThe residue was chromatographed on silica gel eluting with ethylacetate

Sources & evidence

ORD record
ord-619ad07a0dec446781c5f1d25d72c546
Source dataset
uspto-grants-2012_11
Patent number
US08309578B2

Reaction notes

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