Cyclopropylamine → HCID 60687398, compound

HRID 624941Notes

Reaction equation

HRID 624941 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.Cl[CH2:6][C:7]1[O:8][C:9]([CH3:12])=[N:10][N:11]=1>>[CH:1]1([NH:4][CH2:6][C:7]2[O:8][C:9]([CH3:12])=[N:10][N:11]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 38266202-(Chloromethyl)-5-methyl-1,3,4-oxadiazole

Product 1

HCID 60687398HCID 60687398, compoundYield 35%

Procedure

A mixture of cyclopropanamine (765-30-0, 194 mg, 236 μL, 3.39 mmol) and 2-(chloromethyl)-5-methyl-1,3,4-oxadiazole (3914-42-9, 90 mg, 679 μmol) was stirred for 16 h at ambient temperature. The mixture was concentrated under reduced pressure and the residue taken up in ice-water/saturated aqueous Na2CO3 solution 1/1 (20 mL) and EtOAc (30 mL). The layers were separated and the aqueous layer was extracted one more time with EtOAc (30 mL). The combined extracts were washed with ice-water/brine 1/1 (15 mL), dried over Na2SO4 and brought to dryness to give the title compound (36 mg, 35%) as yellow oil which was sufficiently pure to be used in the next reaction step; MS (EI): m/e=154.2 [MH+].

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted one more time with EtOAc (30 mL)
  4. washThe combined extracts were washed with ice-water/brine 1/1 (15 mL)
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-3c4adc099e424416aac687fa0df31c0b
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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