Triethylamine → HCID 13487103, compound

HRID 1975407Notes

Reaction equation

HRID 1975407 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.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC.C1COCC1>[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

7

Reactant 4

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

Product 1

HCID 13487103HCID 13487103, compoundYield 42.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Propionyl chloride (0.49 g, 5.2 mmol) in dry ether (10 ml) was added to a solution of cis-5-methoxy-1-methyl-2-(n-propylamino)tetralin (350 mg, 1.5 mmol) and triethylamine (0.49 g, 4.9 mmol) in dry ether (80 ml). After 30 min. at room temperature the reaction mixture was filtered and the ether was evaporated. The resulting crude amide was passed through an alumina column eluted with ether. The purified amide dissolved in dry THF (20 ml) was added to a suspension of LiAlH4 (1.0 g, 26 mmol) in dry THF (30 ml) under N2. After stirring under reflux for 3 h, the reaction mixture was hydrolyzed, the precipitate was filtered off and the solvent was evaporated. The oily residue was chromatographed on an alumina column with ether-light petroleum (1:1) as eluant. The hydrochloride was prepared and recrystallized from EtOH-ether to give 200 mg (42%) of title product: mp 170.5°-171.5° C.; GC (215° C.) isomeric purity >95%, retention time 2.45 min; NMR (MeOH-d4) δ1.05 (t,6H) δ1.32 (d,3H) δ1.64-3.66 (m,14H), δ3.80 (s,3H), δ6.71-6.82 (m,2H), δ7.10-7.20 (m,1H); MS (70 eV) m/z 275 (28%), 246 (100%), 176 (69%).

Workup

  1. filtrationAfter 30 min. at room temperature the reaction mixture was filtered
  2. customthe ether was evaporated
  3. washeluted with ether
  4. dissolutionThe purified amide dissolved in dry THF (20 ml)
  5. temperatureunder reflux for 3 h
  6. filtrationthe precipitate was filtered off
  7. customthe solvent was evaporated
  8. customThe oily residue was chromatographed on an alumina column with ether-light petroleum (1:1) as eluant
  9. customThe hydrochloride was prepared
  10. customrecrystallized from EtOH-ether

Sources & evidence

ORD record
ord-07a142feb20742f28882542b0c7a0ee0
Source dataset
uspto-grants-1994_02
Patent number
US05286747

Reaction notes

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