Triethylamine → HCID 86746874, compound

HRID 249459Notes

Reaction equation

HRID 249459 reaction equation
[CH:1]1([C:4]([Cl:6])=O)[CH2:3][CH2:2]1.[CH3:7][O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][C@H:13]([NH:20][CH2:21][CH:22]1[CH2:24][CH2:23]1)[C@@H:14]2[CH3:19].C(N(CC)CC)C>CCOCC>[ClH:6].[CH3:7][O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][C@H:13]([N:20]([CH2:4][CH:1]1[CH2:2][CH2:3]1)[CH2:21][CH:22]1[CH2:24][CH2:23]1)[C@@H:14]2[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 18652063HCID 18652063, compound

Product 1

HCID 86746874HCID 86746874, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Cyclopropanecarboxylic acid chloride (0.49 g) in dry ether (10 ml) is added to a solution of cis-5-methoxy-1-methyl-2-(N-cyclopropylmethylamino)tetralin (400 mg) and triethylamine (0.49 g) in dry ether (80 ml). After 30 minutes at room temperature the reaction mixture is filtered and the ether is evaporated. The resulting crude amide is passed through an alumina column eluted with ether. The purified amide dissolved in dry THF (20 ml) is added to a suspension of lithium aluminum hydride (1.0 g) in dry THF (30 ml) under N2. After stirring under reflux for 3 hours, the reaction mixture is hydrolyzed, the precipitate is filtered off and the solvent is evaporated. The oily residue is chromatographed on an alumina column with ether-light petroleum (1:1). The hydrochloride is prepared and recrystallized from ethanol-ether to give the title compound.

Workup

  1. filtrationAfter 30 minutes at room temperature the reaction mixture is filtered
  2. customthe ether is evaporated
  3. washeluted with ether
  4. dissolutionThe purified amide dissolved in dry THF (20 ml)
  5. additionis added to a suspension of lithium aluminum hydride (1.0 g) in dry THF (30 ml) under N2
  6. temperatureunder reflux for 3 hours
  7. filtrationthe precipitate is filtered off
  8. customthe solvent is evaporated
  9. customThe oily residue is chromatographed on an alumina column with ether-light petroleum (1:1)
  10. customThe hydrochloride is prepared
  11. customrecrystallized from ethanol-ether

Sources & evidence

ORD record
ord-351ed40bc4b04385b18fb476bb1e1da9
Source dataset
uspto-grants-1993_05
Patent number
US05214156

Reaction notes

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