Hydrazine hydrate (1:1) → (S)-N-(pyrrolidin-3-yl)-1-adamantanecarboxamide

HRID 992270Notes

Reaction equation

HRID 992270 reaction equation
C([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]([C:16]23[CH2:25][CH:20]4[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]4)[CH2:17]2)[CH2:23]3)=[O:15])[CH2:9]1)C1C=CC=CC=1.O.NN>C(O)C.[C].[Pd]>[NH:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]([C:16]23[CH2:25][CH:20]4[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]4)[CH2:17]2)[CH2:23]3)=[O:15])[CH2:9]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 9884297(S)-N-(1-Benzylpyrrolidin-3-yl)-1-adamantanecarboxamide

Product 1

HCID 49760538(S)-N-(pyrrolidin-3-yl)-1-adamantanecarboxamideYield 93.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

(S)-N-(1-Benzylpyrrolidin-3-yl)-1-adamantanecarboxamide (10.5 g, described in Example 13) was dissolved in ethanol (100 ml), and 10% palladium-carbon (5 g) was added thereto. The mixture was stirred at room temperature, and to the reaction mixture was added hydrazine monohydrate (1.5 ml). The mixture was stirred under heating for 1 hour. The reaction mixture was cooled to room temperature, and 10% palladium-carbon was filtered off with celite. The filtrate was concentrated, and IPE (isopropyl ether) was added to the obtained residue. The precipitated crystals were collected by filtration to give (S)-N-(pyrrolidin-3-yl)-1-adamantanecarboxamide (7.2 g), melting point 186-188° C.

Workup

  1. stirringThe mixture was stirred
  2. temperatureunder heating for 1 hour
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtration10% palladium-carbon was filtered off with celite
  5. concentrationThe filtrate was concentrated
  6. additionIPE (isopropyl ether) was added to the obtained residue
  7. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-c8a9c210ba084c37aced4ecef5bae1ad
Source dataset
uspto-grants-2002_10
Patent number
US06468998B1

Reaction notes

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