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Gamma-Butyrolactone → 3-(Aminomethyl)-3-methyl-2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidine

HRID 1151
Notes
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Reaction equation

HRID 1151 reaction equation
[C:1]1(=O)O[CH2:4][CH2:3][CH2:2]1.[Cl-].[NH4+].[NH2:9][CH2:10][C:11]([CH2:15][NH2:16])([CH2:13][NH2:14])[CH3:12]>O>[NH2:9][CH2:10][C:11]1([CH3:12])[CH2:15][N:16]2[CH2:4][CH2:3][CH2:2][C:1]2=[N:14][CH2:13]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7302Gamma-ButyrolactoneHCID 25517Ammonium ChlorideHCID 45265302-(Aminomethyl)-2-methyl-1,3-propanediamine

Product 1

HCID 184074873-(Aminomethyl)-3-methyl-2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
250 °C

Procedure

A mixture of 21.03 g (0.24 mol) of γ-butyrolactone and 1.31 g (24 mmol) of ammonium chloride in 114.5 g (0.98 mol) of 1,1,1-tris(aminomethyl)ethane was heated at 250° C. in an autoclave. After 1.5 h, the mixture was cooled and the excess amine and the water formed were removed by distillation. The residue was distilled at 200°-240° C./18 mbar. The yield was 22.0 g (54%) of yellowish oil. The boiling point was 117°-120° C./1 mbar. Other data concerning the product was:

Workup

  1. temperaturethe mixture was cooled

Sources & evidence

ORD record
ord-58e35fa5d3104b07bb1cd637b9c2a80b
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723605

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes