Hydrochloric Acid → 1,2,3,4-Tetrahydrobenzofuro[2,3-c]pyridine hydrochloride

HRID 2106643Notes

Reaction equation

HRID 2106643 reaction equation
[BH4-].[Na+].[CH:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[CH2:6][CH2:5][N:4]=1.[ClH:16]>CO.C(O)(C)C>[ClH:16].[CH2:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[CH2:6][CH2:5][NH:4]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 13441207HCID 13441207, compound

Product 1

HCID 139252361,2,3,4-Tetrahydrobenzofuro[2,3-c]pyridine hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
20 °C

Procedure

9.2 g (240 mmol) of sodium borohydride are added in small portions and in the space of 3 h to a suspension of 8.2 g (47.8 mmol) of 3,4-dihydrobenzofuro[2,3-c]pyridine in 350 ml of methanol. The mixture is stirred for 20 h at 20° C. and the solvent then evaporated off under reduced pressure. The residue is washed with water and the 1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine extracted by means of ethyl acetate. The organic phase is separated off after settling has taken place, dried over sodium sulphale and evaporated under reduced pressure, and the residue is treated with one equivalent of 0.1N hydrochloric acid in isopropyl alcohol. The hydrochloride is isolated and recrystallized in a mixture of isopropyl alcohol and ethanol.

Workup

  1. customthe solvent then evaporated off under reduced pressure
  2. washThe residue is washed with water
  3. extractionthe 1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine extracted by means of ethyl acetate
  4. customThe organic phase is separated off after settling
  5. dry with materialdried over sodium sulphale
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6bdf1a5bdb99431cbcbbbfe0c9e15dc5
Source dataset
uspto-grants-1990_06
Patent number
US04931449

Reaction notes

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