Triethylamine → HCID 59631247, compound

HRID 1431782Notes

Reaction equation

HRID 1431782 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([NH2:14])[CH:10]=[C:11]([NH2:13])[CH:12]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH:22]1([C:25](Cl)=[O:26])[CH2:24][CH2:23]1>C(Cl)Cl>[NH2:14][C:9]1[CH:10]=[C:11]([NH:13][C:25]([CH:22]2[CH2:24][CH2:23]2)=[O:26])[CH:12]=[C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 59631264HCID 59631264, compound

Product 1

HCID 59631247HCID 59631247, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-morpholinobenzene-1,3-diamine (0.074 g, 0.383 mmol), triethylamine (0.080 mL, 0.574 mmol), cyclopropanecarbonyl chloride (0.035 mL, 0.383 mmol), and DCM (2 mL) was stirred at 23° C. for 3 h, then concd. The concentrate was partitioned between EtOAc and water, and the products were extracted twice with 25% 2-propanol in chloroform. The combined organics were dried over magnesium sulfate and concd, affording N-(3-amino-5-morpholinophenyl)cyclopropanecarboxamide as a brown amorphous solid. Mass Spectrum (ESI) m/e=262.2 (M+1).

Workup

  1. customThe concentrate was partitioned between EtOAc and water
  2. extractionthe products were extracted twice with 25% 2-propanol in chloroform
  3. dry with materialThe combined organics were dried over magnesium sulfate and concd

Sources & evidence

ORD record
ord-f7f94c156f2e425e82b04285aeb6bae0
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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