Cyclopropanemethanamine → HCID 21701855, compound

HRID 1459002Notes

Reaction equation

HRID 1459002 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 to 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. temperatureto 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-a885384add754b1ba51506e4ee9a3a8d
Source dataset
uspto-grants-1998_12
Patent number
US05852030

Reaction notes

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