Hydrochloric Acid → (7-Dipropylamino-5,6,7,8-tetrahydro-naphthalen-1-yl)-methanol

HRID 274804Notes

Reaction equation

HRID 274804 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[CH2:9][CH2:8]2)=[O:2].[BH4-].[Na+].Cl>C(O)C.O>[CH2:17]([N:13]([CH2:14][CH2:15][CH3:16])[CH:10]1[CH2:9][CH2:8][C:7]2[C:12](=[C:3]([CH2:1][OH:2])[CH:4]=[CH:5][CH:6]=2)[CH2:11]1)[CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 152304978-Formyl-2-dipropylamino-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 10038313(7-Dipropylamino-5,6,7,8-tetrahydro-naphthalen-1-yl)-methanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 8-formyl-2-dipropylamino-1,2,3,4-tetrahydronaphthalene (1 gm, 3.86 mMol) in ethanol (15 mL) was added sodium borohydride (500 mg, 13.2 mMol), and the solution was stirred for 18 hours at room temperature. The reaction mixture was then diluted with water and made acidic with 10% hydrochloric acid. The aqueous was extracted once with diethyl ether, and the organic phase was discarded. The remaining aqueous phase was made basic with concentrated ammonium hydroxide and extracted with dichloromethane. The combined extracts were dried over sodium sulfate and concentrated in vacuo to give a colorless oil. Purification by flash chromatography (3% methanol in dichloromethane+tr. NH4OH) gave the title compound as a colorless, viscous oil (780 mg 77%). The fumarate salt was formed and crystallized (ethanol/diethyl ether) to give colorless crystals (m.p.=151°-152° C.).

Workup

  1. extractionThe aqueous was extracted once with diethyl ether
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a colorless oil
  6. customPurification by flash chromatography (3% methanol in dichloromethane+tr. NH4OH)

Sources & evidence

ORD record
ord-c39182904dba4d5398e1cc6e1dea577b
Source dataset
uspto-grants-1995_02
Patent number
US05389687

Reaction notes

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