Triethylamine → HCID 53895683, compound

HRID 487115Notes

Reaction equation

HRID 487115 reaction equation
[CH2:1]1[C@@H:10]2[C@H:5]([CH2:6][CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[CH2:4][NH:3][CH2:2]1.C(N(CC)CC)C.[O:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[C:27](Cl)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>ClCCl.C1COCC1>[CH2:27]([N:3]1[CH2:2][CH2:1][C@@H:10]2[C@H:5]([CH2:6][CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[CH2:4]1)[C:23]1[O:22][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 21226445Aluminium lithium hydrideHCID 54260071HCID 54260071, compound

Product 1

HCID 53895683HCID 53895683, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure of Example 16, 0.168 g (0.897 mmol) of trans-1,2,3,4,4a,5,6,10b-octahydrobenz[f]isoquinoline in 8 ml of anhydrous dichloromethane was reacted with 0.313 ml (2.25 mmol) of triethylamine and 0.177 ml (1.80 mmol) of 2-furoyl chloride for 11/2 h, then with 2.7 ml of a 1.0M solution of lithium aluminium hydride in THF for 30 minutes at room temperature and 1 h at reflux. Chromatography on flash silica, eluting with 30-40% ethyl acetate/petroleum ether, afforded 0.091 g (38%) of the title product as a white solid. The hydrochloride salt was made using ethereal hydrogen chloride. Upon evaporation of the solvent the title product hydrochloride was obtained as a white solid, m.p. 214°-223° C. (dec). NMR δ(D2O) 1.55 (1H, m), 1.68 (1H, m), 1.79-1.90 (2H, m), 2.62-2.75 (2H, m), 2.91-2.99 (3 H, m), 3.23 (1H, t, J=11.8 Hz), 3.54 (1H, m), 3.72 (1H, m), 4.44 (2H, s), 6.57 (1H, d of d, J=3.3 and 1.9 Hz), 6.75 (1H, d, J=3.2 Hz), 7.21-7.28 (3H, m), 7.33-7.36 (1H, m), 7.67 (1H, d, J=1.8 Hz). m/z (CI+, NH3) 268 (M+H)+, 200 (M-C4H3O)+, 124, 96, 81.

Workup

  1. temperature1 h at reflux
  2. washChromatography on flash silica, eluting with 30-40% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-54a02be2751b45d091a2e8432ab7c61d
Source dataset
uspto-grants-1994_03
Patent number
US05294618

Reaction notes

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