Water → HCID 18357387, compound

HRID 428342Notes

Reaction equation

HRID 428342 reaction equation
[CH:1]([N:4]([CH:17]([CH3:19])[CH3:18])[CH2:5][CH2:6][CH:7]([C:14](=[O:16])[NH2:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].[CH2:20](OC(Cl)C[Cl:25])[CH3:21].O>C(O)=O>[ClH:25].[CH:17]([N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][CH:7]([C:14]1[O:16][CH:20]=[CH:21][N:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 79077Ethane, 1,2-dichloro-1-ethoxy-HCID 18357377HCID 18357377, compound

Product 1

HCID 18357387HCID 18357387, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of N,N-diisopropyl-3-carbamoyl-3-phenylpropanamine, prepared in Example 34.2 (4.05 g, 15.4 mmol), 1,2-dichloroethyl ethyl ether (2,32 g, 16.2 mmol), water (0.300 g, 16.6 mmol) and formic acid (50 mL) was stirred at 75° C. for 3 hours. The formic acid was evaporated and the residue was dissolved in water/diethyl ether. The aqueous phase was made alkaline (11 M NaOH) and extracted twice with diethyl ether. The combined organic phases were dried (Na2SO4) and the solvent evaporated. The crude product was chromatographed on silica (petroleum ether-triethylamine 97:3). The pure amine was precipitated as hydrochloride salt with HCl-saturated diethyl ether, affording the title compound as white crystals, 0.61 g (12%): mp 157-158° C.; 1H NMR (DMSO(d6)) δ1.11 (m, 12H), 2.35 (m, 1H), 2.63 (m, 1H), 3.03 (m, 2H), 3.56 (m, 2H), 4.45 (m, 1H), 7.21-7.40 (m, 6H) 8.06 (d, 1H), 10.20 (br, 1H).

Workup

  1. customThe formic acid was evaporated
  2. dissolutionthe residue was dissolved in water/diethyl ether
  3. extractionextracted twice with diethyl ether
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. customthe solvent evaporated
  6. customThe crude product was chromatographed on silica (petroleum ether-triethylamine 97:3)
  7. customThe pure amine was precipitated as hydrochloride salt with HCl-saturated diethyl ether

Sources & evidence

ORD record
ord-f82f9b616459410198fc97cb47358995
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

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