Sodium Cyanide → HCID 68967602, compound

HRID 2116411Notes

Reaction equation

HRID 2116411 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([O:30][CH3:31])[CH:20]=[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])[C:15]=3[O:14]2)(=O)=O)=CC=1.[C-:32]#[N:33].[Na+]>CS(C)=O>[CH3:31][O:30][C:19]1[CH:20]=[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH3:29])[C:15]2[O:14][CH:13]([CH2:12][C:32]#[N:33])[CH2:17][C:16]=2[CH:18]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 86599372HCID 86599372, compound

Product 1

HCID 68967602HCID 68967602, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (±)-[5-methoxy-7-(2-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (0.25 g, 0.57 mmol) in dimethylsulfoxide (20 mL) was added sodium cyanide (0.07 g, 1.43 mmol) and the reaction mixture was allowed to stir at 50° C. for 1 h. The reaction was quenched by the addition of water (10 mL) and extracted with ethyl acetate (2×10 mL). The combined organics were washed with water (3×20 mL), saturated aqueous sodium chloride (20 mL), dried (magnesium sulfate) and the solvent was removed in vacuo to give a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 2:8) gave (±)-[5-methoxy-7-(2-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]acetonitrile as a colorless oil. The oil was dissolved in ethanol (30 mL), 28% aqueous ammonium hydroxide (20 mL), and treated with rhodium on alumina (0.1 g, 5 wt. %) generally according to procedure described for Example 1 to afford 0.025 g (13%) of (±)-{2-[5-methoxy-7-(2-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]ethyl}amine as a yellow solid, hydrochloride salt. mp 240-242° C.

Workup

  1. customThe reaction was quenched by the addition of water (10 mL)
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. washThe combined organics were washed with water (3×20 mL), saturated aqueous sodium chloride (20 mL)
  4. dry with materialdried (magnesium sulfate)
  5. customthe solvent was removed in vacuo
  6. customto give a crude oil
  7. customPurification by flash column chromatography (silica, ethyl acetate:hexanes 2:8)

Sources & evidence

ORD record
ord-efb278eda11c4b37b38b7ea811b60e0e
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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