Chloroacetonitrile → HCID 18793519, compound

HRID 1004765Notes

Reaction equation

HRID 1004765 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([CH3:18])[CH2:16][NH2:17])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:20][C:21]#[N:22].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([CH3:18])[CH2:16][NH:17][CH2:20][C:21]#[N:22])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 10340Sodium CarbonateHCID 22456836HCID 22456836, compound

Product 1

HCID 18793519HCID 18793519, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (±)-3-(cyclopentyloxy)-4-methoxy-β-methylbenzeneethanamine (0.029 mol), chloroacetonitrile (0.0146 mol) and sodium carbonate (0.0219 mol) in DMF (200 ml) was stirred for 5 hours at 60° C. The reaction mixture was filtered and the filtrate was evaporated. The residue was washed with water, then extracted with 2-methoxy-2-methylpropane. The separated organic layer was dried, filtered, and the solvent was evaporated. The residue was purified by open column chromatography over silica gel (eluent: CH2Cl2 ; CH2Cl2 /2-propanone 96/4, and 90/10; then, CH2Cl2 /CH3OH 80/20). The pure fractions were collected and the solvent was evaporated, yielding 3.24 g (77%) of (±)-[[2-[3-(cyclopentyloxy)-4-methoxyphenyl]propyl]amino]acetonitrile (intermediate 21).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. washThe residue was washed with water
  4. extractionextracted with 2-methoxy-2-methylpropane
  5. customThe separated organic layer was dried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by open column chromatography over silica gel (eluent
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6ea8e2ffb28a498db27bcb923a9a3a8e
Source dataset
uspto-grants-2000_04
Patent number
US06051718

Reaction notes

Loading…