2,5-Hexanedione → 3-(2,5-Dimethylpyrrolidin-1-yl)propan-1-ol

HRID 1979907Notes

Reaction equation

HRID 1979907 reaction equation
[CH3:1][C:2](=O)[CH2:3][CH2:4][C:5](=O)[CH3:6].[NH2:9][CH2:10][CH2:11][CH2:12][OH:13]>[Pd].C(O)C>[OH:13][CH2:12][CH2:11][CH2:10][N:9]1[CH:2]([CH3:1])[CH2:3][CH2:4][CH:5]1[CH3:6]

Participants

5

Reactant 2

HCID 80352,5-HexanedioneHCID 90863-Amino-1-propanol

Product 1

HCID 1027123-(2,5-Dimethylpyrrolidin-1-yl)propan-1-olYield 36%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A total of 3 moles of 2,5-hexanedione, 3 moles of 3-amino-1propanol, 10 g of 10% Pd/C, and 500 ml of ethanol were charged to an autoclave. The reaction mixture was pressured up to 1100 psi of H2 and kept for 3 hours at 100° C. Distillation yielded 170 g of N-(3-hydroxypropyl)-2,5-dimethylpyrrolidine (b.p.=119° C. at 25 mm).

Workup

  1. distillationDistillation

Sources & evidence

ORD record
ord-9b81856340254beda417e4d710f7b50b
Source dataset
uspto-grants-1984_11
Patent number
US04483833

Reaction notes

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