Hydrochloric Acid → HCID 68962559, compound

HRID 2116103Notes

Reaction equation

HRID 2116103 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CO[C:9](=O)[NH:10][CH2:11][CH:12]1[CH2:16][C:15]2[CH:17]=[C:18]([Cl:27])[CH:19]=[C:20]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:14]=2[O:13]1.Cl>O1CCCC1>[Cl:27][C:18]1[CH:19]=[C:20]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:14]2[O:13][CH:12]([CH2:11][NH:10][CH3:9])[CH2:16][C:15]=2[CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 86601826HCID 86601826, compound

Product 1

HCID 68962559HCID 68962559, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (0.114 g, 3.0 mmol) in tetrahydrofuran (30 mL) was added (±)-methyl(5-chloro-7-cyclohexyl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate (0.65 g, 2.0 mmol) and the reaction mixture was allowed to stir at room temperature for 30 h. The reaction mixture was quenched with saturated ammonium chloride (50 mL), diluted with tetrahydrofuran (70 mL), and the aqueous layer was extracted with tetrahydrofuran (2×50 mL). The combined organic layers were washed with saturated aqueous sodium bicarbonate (100 mL) and saturated aqueous sodium chloride (100 mL), were dried (sodium sulfate), and the solvent was removed in vacuo to provide a crude oil. Purification by flash column chromatography (silica, dichloromethane:methanol 97:3) gave a light brown oil. The oil was re-dissolved in tetrahydrofuran (50 mL) and aqueous hydrogen chloride (1 N, 3 mL) was added. The resulting precipitate was filtered and washed with diethyl ether to provide 0.28 g (44%) of (±)-N-[(5-chloro-7-cyclohexyl-2,3-dihydro-1-benzofuran-2-yl)methyl]-N-methylamine as a white solid, hydrochloride salt. mp 125-128° C.; Anal. calcd. for C16H22ClNOHCl: C, 60.76; H, 7.33; N, 4.43. Found: C, 60.92; H, 7.46; N, 4.09.

Workup

  1. customThe reaction mixture was quenched with saturated ammonium chloride (50 mL)
  2. additiondiluted with tetrahydrofuran (70 mL)
  3. extractionthe aqueous layer was extracted with tetrahydrofuran (2×50 mL)
  4. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate (100 mL) and saturated aqueous sodium chloride (100 mL)
  5. dry with materialwere dried (sodium sulfate)
  6. customthe solvent was removed in vacuo
  7. customto provide a crude oil
  8. customPurification by flash column chromatography (silica, dichloromethane:methanol 97:3)
  9. customgave a light brown oil
  10. filtrationThe resulting precipitate was filtered
  11. washwashed with diethyl ether

Sources & evidence

ORD record
ord-36300be5cd85417b9b093a201741e464
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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