1-Pyrrolidinamine → Aminopyrrolizine

HRID 1601646Notes

Reaction equation

HRID 1601646 reaction equation
[H][H].[NH:3]1[CH:8]=[CH:7][CH2:6][CH:5]([CH2:9]O)N1.N1C=C[CH2:14][CH2:13]N1.[NH:17]1CCCCN1.[NH2:23][N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1.N1CCCC1>[Pd].CO>[NH2:17][CH:6]1[C:5]2[N:3]([CH:13]=[CH:14][CH:9]=2)[CH:8]=[CH:7]1.[NH:24]1[CH:28]=[CH:27][CH2:26][CH2:25][NH:23]1

Participants

10

Reactant 6

HCID 279461-Pyrrolidinamine2×HCID 31268PyrrolidineHCID 1363341,2-Diazinane3×HCID 21255899Tetrahydropyridazine3×HCID 86754750Tetrahydropyridazine methanolHCID 178418361HCID 178418361, compound

Product 2

HCID 21255897AminopyrrolizineHCID 21255899Tetrahydropyridazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A reactor was charged with 0.0675 g of 5% palladium/carbon and 3.9 g of methanol, hydrogen substitution was carried out, and the catalyst was activated. Then, 2.8 g of a tetrahydropyridazine methanol solution [composition: tetrahydropyridazine 23.77% by weight, 0.67 g (0.008 mole), pyrrolidine 1.61% by weight, 0.05 g (0.0006 mole), 1-aminopyrrolidine 1.36% by weight, 0.04 g (0.0004 mole)] was added to adjust it to a 10% by weight methanol solution of tetrahydropyridazine. Thereafter, at room temperature, a catalytic hydrogenation reaction was carried out under a normal pressure for 5 days. After the reaction, the reaction solution was analyzed by GC. The results were as follows: Hexahydropyridazine 46.98%, tetrahydropyridazine 22.84%, 1-aminopyrrolidine 23.89%, and pyrrolidine 3.91%, and the formation of hexahydropyridazine as the intended product was confirmed. The reaction selectivity was hexahydropyridazine 60.89%, 1-aminopyrrolidine 30.96%, and the conversion of tetrahydropyridazine was 77.16%. Incidentally, 1-aminopyrrolizine was formed from tetrahydropyridazine by a reduction side reaction, and the formation of pyrrolidine as a decomposition product was recognized.

Workup

  1. customThereafter, at room temperature, a catalytic hydrogenation reaction
  2. customAfter the reaction

Sources & evidence

ORD record
ord-1aaf00534df84e64a57c465a72e9f334
Source dataset
uspto-grants-1999_11
Patent number
US05977360

Reaction notes

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