Hydrochloric Acid → HCID 68964265, compound

HRID 2116272Notes

Reaction equation

HRID 2116272 reaction equation
CC1C=CC(S(O[CH:12]2[CH2:16][C:15]3[CH:17]=[CH:18][CH:19]=[C:20]([C:21]4[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:28])[C:14]=3[O:13]2)(=O)=O)=CC=1.[CH2:29]([NH2:31])[CH3:30].Cl.[CH3:33]S(C)=O>O.C(OCC)(=O)C.C(O)(C)C>[Cl:27][C:26]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:28])[C:21]=1[C:20]1[C:14]2[O:13][CH:12]([CH2:33][NH:31][CH2:29][CH3:30])[CH2:16][C:15]=2[CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 6341EthylamineHCID 86599283HCID 86599283, compound

Product 1

HCID 68964265HCID 68964265, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (±)-7-(2,6-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl 4-methylbenzenesulfonate (0.2 g, 0.46 mmol) in dimethylsulfoxide (5 mL) was added ethylamine (0.20 g, 4.4 mmol) and the reaction mixture was allowed to stir at 60° C. for 12 h. The reaction was diluted with water (10 mL) and ethyl acetate (2×10 mL). The combined organic layers were washed with water (3×20 mL) and saturated aqueous sodium chloride (20 mL), dried (magnesium sulfate) and the solvent was removed in vacuo to give an oil. The oil was re-dissolved in isopropanol (0.5 mL) and hydrogen chloride (0.5 mL, 1.0 M in diethyl ether) was added. The resulting precipitate was filtered, washed (diethyl ether), to give 0.084 g (57%) of (±)-N-{[7-(2,6-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}ethanamine as a white solid, hydrochloride salt. mp 195-197° C.

Workup

  1. washThe combined organic layers were washed with water (3×20 mL) and saturated aqueous sodium chloride (20 mL)
  2. dry with materialdried (magnesium sulfate)
  3. customthe solvent was removed in vacuo
  4. customto give an oil
  5. filtrationThe resulting precipitate was filtered
  6. washwashed (diethyl ether)

Sources & evidence

ORD record
ord-0d2522c4fc5b450e889c0e207960839a
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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