Cyclopropanemethanamine → HCID 57956063, compound

HRID 561817Notes

Reaction equation

HRID 561817 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][O:12][CH3:13])=[CH:6][C:3]=1[CH:4]=O.[CH:14]1([CH2:17][NH2:18])[CH2:16][CH2:15]1.C(=O)(O)[O-].[Na+].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][O:12][CH3:13])=[CH:6][C:3]=1[CH2:4][NH:18][CH2:17][CH:14]1[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 75646CyclopropanemethanamineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86635909HCID 86635909, compound

Product 1

HCID 57956063HCID 57956063, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-chloro-5-(2-methoxyethyl)benzaldehyde from Amine 7, Step 6 (1 eq.) in methanol (0.8 M) was added 1-cyclopropylmethanamine (1.2 eq.) and sodium bicarbonate (1.5 eq). The vessel was sealed and heated at 70° C. for 2 h. The insolubles were removed via filtration and to the filtrate was then added sodium borohydride (1.5 eq.) at 0° C. The reaction mixture was allowed to warm slowly to RT overnight. The volatiles were removed in vacuo and the resulting residue was partitioned between 1 N aq. NaOH and ether. The aqueous layer was separated and back extracted with ether. The combined ethereal extracts were washed with brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound.

Workup

  1. customThe vessel was sealed
  2. customThe insolubles were removed via filtration and to the filtrate
  3. customat 0° C
  4. temperatureto warm slowly to RT overnight
  5. customThe volatiles were removed in vacuo
  6. customthe resulting residue was partitioned between 1 N aq. NaOH and ether
  7. customThe aqueous layer was separated
  8. extractionback extracted with ether
  9. washThe combined ethereal extracts were washed with brine
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered

Sources & evidence

ORD record
ord-e559a8d3520541dd96c107ce37cef0b1
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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