Cyclopropanemethanamine → HCID 68906158, compound

HRID 1785734Notes

Reaction equation

HRID 1785734 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:28]([F:31])([F:30])[F:29])=[C:11]([CH2:15][O:16][CH:17]3[CH2:20][N:19]([C:21]([NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]3)[CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.[CH:32]1([CH2:35][NH2:36])[CH2:34][CH2:33]1>>[CH:32]1([CH2:35][NH:36][CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[C:10]([C:28]([F:31])([F:30])[F:29])=[C:11]([CH2:15][O:16][CH:17]4[CH2:20][N:19]([C:21]([NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]4)[CH:12]=[CH:13][CH:14]=3)=[CH:5][CH:4]=2)[CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 75646CyclopropanemethanamineHCID 68907467HCID 68907467, compound

Product 1

HCID 68906158HCID 68906158, compoundYield 98%

Procedure

The benzyl chloride (195) (34 mg, 0.075 mmol) and cyclopropylmethylamine (1 mL, 12 mmol) were heated to 50° C. for 18 h. The reaction mixture was cooled, excess amine was removed under reduced pressure and the residue partitioned between ethyl acetate and sodium hydroxide (1M). The organic phase was washed with water (2×20 mL) and brine (20 mL), dried (Na2SO4), filtered and the solvent removed under reduced pressure to afford the crude product. Purification by SCX-2 cartridge afforded the title compound (197) as a colourless gum (36 mg, 98% yield).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customexcess amine was removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate and sodium hydroxide (1M)
  4. washThe organic phase was washed with water (2×20 mL) and brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customto afford the crude product
  9. customPurification by SCX-2 cartridge

Sources & evidence

ORD record
ord-95d2b18bc88b41818ace71d5bb059c8e
Source dataset
uspto-grants-2009_03
Patent number
US07504522B2

Reaction notes

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