1,3-Propanediamine → HCID 58406354, compound

HRID 1753119Notes

Reaction equation

HRID 1753119 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][N:10]2[CH:14]=[CH:13][CH:12]=[C:11]2[C:15]([O:17]C)=O)=[CH:4][CH:3]=1.[CH2:20]([NH2:24])[CH2:21][CH2:22][NH2:23]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[CH2:9][N:10]4[CH:14]=[CH:13][CH:12]=[C:11]4[C:15](=[O:17])[N:23]2[CH2:22][CH2:21][CH2:20][NH:24]3)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 4281,3-PropanediamineHCID 13154205HCID 13154205, compound

Product 1

HCID 58406354HCID 58406354, compoundYield 10.6%

Conditions

Temperature
180 °C

Procedure

Methyl 1-[2-(4-chlorophenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylate (100 mg, 0.36 mmol) was mixed with propane-1,3-diamine (0.9 g, 12.14 mmol) in xylenes (2 mL) and the mixture heated in the microwave at 180° C. for 1 hour (monitored by LCMS). The mixture was concentrated in vacuo and purified by flash chromatography using 2 to 10% MeON in CH2Cl2, to give 11a-(4-chlorophenyl)-1,2,3,4,11,11a-hexahydro-6H-pyrrolo[1′,2′:4,5]pyrazino[1,2-a]pyrimidin-6-one (123) (11.5 mg, yield 10%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-d5efbb8bfe534704ac9d9e94f9cd4c25
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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