Cyclopropanemethanamine → HCID 21701855, compound

HRID 2288052Notes

Reaction equation

HRID 2288052 reaction equation
[C:1]([O:5][C:6]([NH:8][NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:19]1([CH2:22][NH2:23])[CH2:21][CH2:20]1.Cl.CN(C)CCCN=C=NCC>ClCCl>[C:1]([O:5][C:6]([NH:8][NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:12]([C:13](=[O:15])[NH:23][CH2:22][CH:19]2[CH2:21][CH2:20]2)[CH:11]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 75646CyclopropanemethanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 217018073-[2-(tert-Butoxycarbonyl)hydrazinyl]benzoic acid

Product 1

HCID 21701855HCID 21701855, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 4.40 g of unpurified 3-(2-tert-butoxycarbonylhydrazino)benzoic acid was dissolved in 80 ml of dichloromethane. To this mixture, 1.78 g of cyclopropylmethylamine and 3.45 g of 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloric acid salt were added and the resulting mixture was heated at reflux for 2 hours. After leaving the reaction mixture to cool to room temperature, the mixture was sequentially washed with 50 ml of water, 50 ml of 1N hydrochloric acid and then 50 ml of aqueous saturated sodium hydrogen carbonate solution, dried and concentrated to obtain 3.42 g of crude crystals. The crude crystals were recrystallized twice from ethyl acetate-hexane to obtain 1.29 g (yield 40%, three steps) of the captioned compound.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 2 hours
  3. customAfter leaving the reaction mixture
  4. washthe mixture was sequentially washed with 50 ml of water, 50 ml of 1N hydrochloric acid
  5. dry with material50 ml of aqueous saturated sodium hydrogen carbonate solution, dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d435eb1708b549a2a9dc0a469a2f1b45
Source dataset
uspto-grants-2000_07
Patent number
US06087369

Reaction notes

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