Water → N-((1-Benzylpyrrolidin-3-yl)methyl)cyclopropanamine

HRID 978563Notes

Reaction equation

HRID 978563 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O=[C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH:10]([C:20]([NH:22][CH:23]2[CH2:25][CH2:24]2)=O)[CH2:9]1.O.[OH-].[Na+]>O1CCCC1>[C:14]1([CH2:13][N:12]2[CH2:8][CH2:9][CH:10]([CH2:20][NH:22][CH:23]3[CH2:25][CH2:24]3)[CH2:11]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 134918001-Benzyl-N-cyclopropyl-5-oxopyrrolidine-3-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 14280886N-((1-Benzylpyrrolidin-3-yl)methyl)cyclopropanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 8.2 g (0.20 mole) of lithium aluminum hydride in 150 ml of dry tetrahydrofuran was added portionwise 18.0 g (70.0 mmole) of solid 5-oxo-1-(phenylmethyl)-N-cyclopropyl-3-pyrrolidinecarboxamide. When the addition was complete, the reaction mixture was stirred at room temperature for 18 hours and then at reflux for two hours. After cooling to room temperature, the mixture was treated dropwise, successively, with 8 ml of water, 8 ml of 15% aqueous sodium hydroxide and 24 ml of water, titrating the final addition to produce a granular precipitate. The solid was removed by filtration, washed with tetrahydrofuran and the filtrate evaporated in vacuo to give 16.0 g of 1-(phenylmethyl)-N-cyclopropyl-3-pyrrolidinemethanamine, as a heavy oil. This was used for the next step without further purification.

Workup

  1. additionWhen the addition
  2. temperatureat reflux for two hours
  3. temperatureAfter cooling to room temperature
  4. additionthe mixture was treated dropwise
  5. additionaddition
  6. customto produce a granular precipitate
  7. customThe solid was removed by filtration
  8. washwashed with tetrahydrofuran
  9. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-4cdefa6152784491aacb3d3163947326
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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