Cyclopropylamine → HCID 53714022, compound

HRID 342233Notes

Reaction equation

HRID 342233 reaction equation
[CH:1]1([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH:2]1[C:4]([O-])=[O:5].[CH:11]1([NH2:14])[CH2:13][CH2:12]1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C1C=CC=CN=1)C>[CH:11]1([NH:14][C:4]([CH:2]2[CH2:3][CH:1]2[C:7]([O:9][CH3:10])=[O:8])=[O:5])[CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 69828CyclopropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20026542HCID 20026542, compound

Product 1

HCID 53714022HCID 53714022, compound

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 9.3 g of monomethyl (1RS,2RS)-1,2-cyclopropanedicarboxylate, 4.0 ml of N-cyclopropylamine and 11.6 g of N(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride in 210 ml of methylene chloride is treated at 0° C. with 0.7 g of dimethylaminopyridine and subsequently stirred at room temperature for 2 hrs. The reaction solution is worked-up with methylene chloride/10% potassium hydrogen sulphate solution. The organic phase is washed with saturated sodium bicarbonate solution, dried and concentrated to give 10.6 g of methyl (1RS,2RS)-2-cyclopropylcarbamoyl-cyclopropanecarboxylate.

Workup

  1. washThe organic phase is washed with saturated sodium bicarbonate solution
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7c589cec6ca940ea890745d8e15057f5
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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