Triethylamine → HCID 13487103, compound

HRID 1975408Notes

Reaction equation

HRID 1975408 reaction equation
[C:1]([Cl:5])(=O)[CH2:2][CH3:3].[CH3:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][C@H:12]([NH:19][CH2:20][CH2:21][CH3:22])[C@@H:13]2[CH3:18].C(N(CC)CC)C.[Cl-].C([NH+](CC)CC)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC.O1CCCC1>[ClH:5].[CH3:6][O:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][C@H:12]([N:19]([CH2:1][CH2:2][CH3:3])[CH2:20][CH2:21][CH3:22])[C@@H:13]2[CH3:18]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 12698378Triethylazanium chlorideHCID 13755574HCID 13755574, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13487103HCID 13487103, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Propionylchloride (0.28 g, 0.0030 mol) in dry ether (5 ml) was slowly added at 5° C. to a solution of (-)-cis-5-methoxy-1-methyl-2-(n-propylamino)tetralin (0.35 g, 0.0015 mol), triethylamine (0.31 g, 0.0030 mol) and dry ether (45 ml). The mixture was stirred at room temperature for 1 hour, whereupon the triethylammoniumchloride formed was filtered off and the solvent evaporated. The residue (0.40 g) dissolved in dry tetrahydrofuran (10 ml) was added to a suspension of LiAlH4 (0.80 g, 0.021 mol) in dry tetrahydrofuran (40 ml) under nitrogen. After stirring under reflux for 5 hours, the mixture was hydrolyzed, the precipitate was filtered off, and the solvent was evaporated. The residue was passed through an alumina column with ether/light petroleum (20:80) as eluant, and the amine was precipitated as the hydrochloride and recrystallized from ethanol-ether to give (-)-cis-5-methoxy-1-methyl-2-(di-n-propylamino)tetralin hydrochloride. (0.37 g, 79%) m.p. 161°-162° C. [α]D22 =-48.2 (c=1.1, CH3OH).

Workup

  1. customformed
  2. filtrationwas filtered off
  3. customthe solvent evaporated
  4. dissolutionThe residue (0.40 g) dissolved in dry tetrahydrofuran (10 ml)
  5. temperatureunder reflux for 5 hours
  6. filtrationthe precipitate was filtered off
  7. customthe solvent was evaporated
  8. customthe amine was precipitated as the hydrochloride
  9. customrecrystallized from ethanol-ether

Sources & evidence

ORD record
ord-2af7453ea5c24dcdbdee2a4679e0a575
Source dataset
uspto-grants-1994_02
Patent number
US05286747

Reaction notes

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