Hydrochloric Acid → (+/-)-1-(5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)-N-methylmethanamine

HRID 13972Notes

Reaction equation

HRID 13972 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:11]2[O:12][CH:13]([CH2:15][NH:16][C:17](=O)OC)[CH2:14][C:10]=2[CH:9]=1.Cl>O1CCCC1>[Cl:7][C:8]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:11]2[O:12][CH:13]([CH2:15][NH:16][CH3:17])[CH2:14][C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 86598556(+/-)-Methyl (5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)methylcarbamate

Product 1

HCID 11288100(+/-)-1-(5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)-N-methylmethanamineYield 23.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of lithium aluminum hydride (95 wt. %, 0.45 g, 11.25 mmol) in tetrahydrofuran (45 mL) was added (±)-methyl (5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)methylcarbamate (1.16 g, 3.98 mmol) and the resulting reaction mixture was allowed to stir at room temperature for 40 h. The reaction mixture was diluted with tetrahydrofuran (150 mL), quenched with saturated ammonium chloride (50 mL), and the organic layer was separated and washed with saturated aqueous sodium bicarbonate (50 mL), saturated aqueous sodium chloride (50 mL), dried (magnesium sulfate), and the solvent was removed in vacuo to provide a crude oil. Purification by flash chromatography (silica, methanol:dichloromethane 1:39) provided a light brown oil. The oil was re-dissolved in tetrahydrofuran (50 mL) and aqueous hydrogen chloride (1.0 N, 1 mL) was added. The resulting precipitate was filtered, washed (diethyl ether), and dried to afford 0.23 g (20%) of (±)-1-(5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)-N-methylmethanamine as a white solid, hydrochloride salt. mp 224-226° C.; Anal. calcd. for C14H14ClNOHCl.0.1H2O: C, 58.80; H, 5.36; N, 4.90. Found: C, 58.65; H, 5.30; N, 4.84.

Workup

  1. customthe resulting reaction mixture
  2. customquenched with saturated ammonium chloride (50 mL)
  3. customthe organic layer was separated
  4. washwashed with saturated aqueous sodium bicarbonate (50 mL), saturated aqueous sodium chloride (50 mL)
  5. dry with materialdried (magnesium sulfate)
  6. customthe solvent was removed in vacuo
  7. customto provide a crude oil
  8. customPurification by flash chromatography (silica, methanol:dichloromethane 1:39)
  9. customprovided a light brown oil
  10. filtrationThe resulting precipitate was filtered
  11. washwashed (diethyl ether)
  12. customdried

Sources & evidence

ORD record
ord-e6758ff63d584d85bddf132dd46294af
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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