Cyclopropylamine → HCID 178453958, compound

HRID 2093921Notes

Reaction equation

HRID 2093921 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:18]1([NH2:21])[CH2:20][CH2:19]1.Cl.CN(C)CCCN=C=NCC>ClCCl>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15](=[O:17])[NH:21][CH:18]2[CH2:20][CH2:19]2)[CH2:13][CH2:14]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178453972HCID 178453972, compound

Product 1

HCID 178453958HCID 178453958, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of trans-4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (6.1 g, 25.0 mmol) and cyclopropylamine (1.9 mL, 27.5 mmol) in dichloromethane (125 mL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.3 g; 27.5 mmol) is added in one portion. The reaction is stirred at ambient temperature for 48 hours. The solvent is evaporated and the crude is stirred in ice-cold 1N hydrochloric acid (100 mL) for 30 min. The solid product is isolated by suction filtration, washed with small portions of water and recrystallized from ethanol/water to deliver 5.2 g of the title compound as colorless solid.

Workup

  1. additionis added in one portion
  2. customThe solvent is evaporated
  3. stirringthe crude is stirred in ice-cold 1N hydrochloric acid (100 mL) for 30 min
  4. customThe solid product is isolated by suction filtration
  5. washwashed with small portions of water
  6. customrecrystallized from ethanol/water

Sources & evidence

ORD record
ord-ec20add82f9d474f9658594109006d33
Source dataset
uspto-grants-2013_05
Patent number
US08445501B2

Reaction notes

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