Hydrochloric Acid → 2,5,6,7,8,9-Hexahydro-1′-methylspiro[3H-furo[2,3-h][1]benzazepine-3,4′-piperidine]

HRID 1741047Notes

Reaction equation

HRID 1741047 reaction equation
C([N:4]1[C:10]2[CH:11]=[C:12]3[C:17]4([CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]4)[CH2:16][O:15][C:13]3=[CH:14][C:9]=2[CH2:8][CH2:7][CH2:6][CH2:5]1)(=O)C.Cl>>[CH3:23][N:20]1[CH2:19][CH2:18][C:17]2([C:12]3=[CH:11][C:10]4[NH:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]=4[CH:14]=[C:13]3[O:15][CH2:16]2)[CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 23225271HCID 23225271, compound

Product 1

HCID 218338512,5,6,7,8,9-Hexahydro-1′-methylspiro[3H-furo[2,3-h][1]benzazepine-3,4′-piperidine]Yield 90.9%

Procedure

5-Acetyl-3,5,6,7,8,9-hexahydro-1'-methylspiro [2H-furo[2,3-h]benzazepine-3,4'-piperidine] (D27, 0.25 g, 0.82 mmol) was stirred at reflux under Ar in c. HCl (15 ml) for 4 days. It was then evaporated to dryness, dissolved in dichloromethane, washed with K2CO3 solution, dried (Na2SO4) and evaporated to give the title compound (0.203 g) as a brown gum, still containing ca. 15% of amide (NMR). Chromatography on silica, eluting with 0-15% methanol in dichloromethane, give purer material (0.107 g, 49%)

Workup

  1. temperatureat reflux under Ar in c
  2. customIt was then evaporated to dryness
  3. dissolutiondissolved in dichloromethane
  4. washwashed with K2CO3 solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-36a98028ef24419a8d74cef7adb7b7b6
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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