Hydrochloric Acid → HCID 20446749, compound

HRID 2417785Notes

Reaction equation

HRID 2417785 reaction equation
Br.[CH2:2]([N:5]([CH2:17][CH2:18][CH3:19])[CH:6]1[CH2:15][C:14]2[C:13]([OH:16])=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8][CH2:7]1)[CH2:3][CH3:4].B(Cl)(Cl)Cl.Cl[CH2:25][C:26]#N.[Cl-].[Cl-].[Cl-].[Al+3].Cl.[OH-:33].[NH4+]>ClCCl.C(Cl)(Cl)Cl>[CH2:17]([N:5]([CH2:2][CH2:3][CH3:4])[CH:6]1[CH2:15][C:14]2[C:13]3[O:16][CH2:25][C:26](=[O:33])[C:12]=3[CH:11]=[CH:10][C:9]=2[CH2:8][CH2:7]1)[CH2:18][CH3:19]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 7856ChloroacetonitrileHCID 14923Ammonium HydroxideHCID 25135Boron TrichlorideHCID 6451240Aluminum(III) ChlorideHCID 69177948-Hydroxy-2-dipropylaminotetralin hydrobromide

Product 1

HCID 20446749HCID 20446749, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

5,6,7,8-Tetrahydro-7-(dipropylamino)-naphthalenol hydrobromide [5.90 g, 18.0 mmol, described by L.-E. Arvidsson et al., J. Med. Chem. 24, 921 (1981)] was added portionwise as a solid to an ice-cold solution of boron trichloride in dichloromethane (43 mL, 1M solution). To the clear solution was added successively chloroacetonitrile (2.74 mL, 43 mmol) and aluminum trichloride (2.88 g, 22 mmol). A precipitate formed after 0.5 hour. The suspension was left stirring at room temperature overnight. Then, ice-water and 10% hydrochloric acid (20 mL) were added and the mixture was stirred vigorously for 1 hour at room temperature. It was made basic with dilute ammonium hydroxide and shaken with chloroform. The emulsion was filtered through diatomaceous earth, and washed with chloroform. The organic layer was separated, dried and evaporated to dryness. The residue was taken up in chloroform (150 mL) and triethylamine (10 mL) was added. The solution was refluxed on a steam bath for 2 hours, and evaporated to dryness. The residue was partitioned between diethyl ether and dilute ammonium hydroxide. The ether phase was washed with water, dried and evaporated to give N,N-dipropyl-2,3,6,7,8,9-hexahydro-3-oxonaphtho[1,2-b]furan-8-amine as a crude pink solid (5.5 g), and was used as such for the next step. An analytical sample was passed through a column of silica gel and eluted with chloroform and a mixture of acetone and chloroform (1:9) to give an oil which solidified on standing: mp 56°-64° C. and NMR (CDCl3)δ 0.87 (t, 6H), 1.47 (m, 6H), 2.48 (t, 4H), 2.70 (m, 1H), 2.87 (m, 4H), 4.59 (s, 2H), 6.27 (d, 1H) and 7.37 (d, 1H).

Workup

  1. customA precipitate formed after 0.5 hour
  2. waitThe suspension was left
  3. stirringthe mixture was stirred vigorously for 1 hour at room temperature
  4. filtrationThe emulsion was filtered through diatomaceous earth
  5. washwashed with chloroform
  6. customThe organic layer was separated
  7. customdried
  8. customevaporated to dryness
  9. additiontriethylamine (10 mL) was added
  10. temperatureThe solution was refluxed on a steam bath for 2 hours
  11. customevaporated to dryness
  12. customThe residue was partitioned between diethyl ether and dilute ammonium hydroxide
  13. washThe ether phase was washed with water
  14. customdried
  15. customevaporated

Sources & evidence

ORD record
ord-494e219516f54364a7c731aa647bbad3
Source dataset
uspto-grants-1984_09
Patent number
US04470990

Reaction notes

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