Potassium Carbonate → N-(2-morpholinoethyl)cyclopropanamine hydrochloride

HRID 625244Notes

Reaction equation

HRID 625244 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[CH:10]1([NH2:13])[CH2:12][CH2:11]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[ClH:1].[O:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][NH:13][CH:10]2[CH2:12][CH2:11]2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69828CyclopropylamineHCID 767274-(2-Chloroethyl)morpholine

Product 1

HCID 67516747N-(2-morpholinoethyl)cyclopropanamine hydrochlorideYield 73.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 100 mg of N-(2-chloroethyl)morpholine and 307 mg of cyclopropylamine in 5 mL of CH3CN was refluxed for 2 h. The mixture was cooled to 25° C. and treated with excess K2CO3. After stirring for 1 h the suspension was filtered and the solvent was evaporated. The residual solvent was removed at high vacuum and the residue was dissolved in a large excess of methanolic HCl. The solvent was evaporated to give 102 mg of the product.

Workup

  1. filtrationwas filtered
  2. customthe solvent was evaporated
  3. customThe residual solvent was removed at high vacuum
  4. dissolutionthe residue was dissolved in a large excess of methanolic HCl
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-0c8e88a0a5794c97a383443ba0b6194c
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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