Hydrochloric Acid → HCID 11960769, compound

HRID 2116190Notes

Reaction equation

HRID 2116190 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[O:15][CH:14]([CH2:17][NH:18]C(=O)OCC3C=CC=CC=3)[CH2:13][C:12]=2[CH:11]=[CH:10][CH:9]=1.I[Si](C)(C)C.Cl>C(#N)C.C(O)(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[O:15][CH:14]([CH2:17][NH2:18])[CH2:13][C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 85247Trimethylsilyl iodideHCID 86599242(+)-Benzyl{[7-(2-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate

Product 1

HCID 11960769HCID 11960769, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (+)-benzyl {[7-(2-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl]carbamate (0.530 g, 1.34 mmol) in acetonitrile (25 mL) cooled to 0° C. was added iodotrimethylsilane (1.07 g, 5.38 mmol) and the reaction mixture was allowed to stir for 90 min. The reaction mixture was quenched by the addition of aqueous hydrogen chloride (25 mL, 2.0 N) and washed with diethyl ether (50 mL). The aqueous layer was neutralized with aqueous sodium hydroxide (50 mL, 2.5 N) and extracted with dichloromethane (2×100 mL). The combined organic fractions were washed with water (75 mL), saturated aqueous sodium chloride (50 mL), dried (magnesium sulfate), and the solvent removed in vacuo to provide a crude oil. The oil was re-dissolved in isopropanol (2 mL) and hydrogen chloride (5.0 mL, 1.0 M in diethyl ether) was added. The resulting precipitate was filtered, washed (diethyl ether), and dried to afford 0.229 g (58%) of (−)-1-[7-(2-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. [α]D25=−11.06 (c 10.0 in dimethylsulfoxide); mp 186-188° C.; Anal. calcd. for C15H14ClNOHCl: C, 60.83; H, 5.1; N, 4.73. Found C, 59.59; H, 5.13; N, 4.48.

Workup

  1. customThe reaction mixture was quenched by the addition of aqueous hydrogen chloride (25 mL, 2.0 N)
  2. washwashed with diethyl ether (50 mL)
  3. extractionextracted with dichloromethane (2×100 mL)
  4. washThe combined organic fractions were washed with water (75 mL), saturated aqueous sodium chloride (50 mL)
  5. dry with materialdried (magnesium sulfate)
  6. customthe solvent removed in vacuo
  7. customto provide a crude oil
  8. filtrationThe resulting precipitate was filtered
  9. washwashed (diethyl ether)
  10. customdried

Sources & evidence

ORD record
ord-11be7a2aa1624d1593f99d535c1d9075
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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