Hydrochloric Acid → HCID 18620599, compound

HRID 1861704Notes

Reaction equation

HRID 1861704 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:26]=[CH:25][C:17]3[CH2:18][CH2:19][CH2:20][N:21](C=O)[CH2:22][C:16]=3[CH:15]=2)=[O:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl>CO>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:26]=[CH:25][C:17]3[CH2:18][CH2:19][CH2:20][NH:21][CH2:22][C:16]=3[CH:15]=2)=[O:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18620594HCID 18620594, compound

Product 1

HCID 18620599HCID 18620599, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
82.5 °C

Procedure

A solution of 3-(1-acetyl-4-piperidinyl)-1-(2-formyl-2,3,4,5-tetrahydro-1H-2-benzazepin-8-yl)-1-propanone (7.03 g, 20.5 mmol), prepared in 1), in methanol (100 ml) was mixed with concentrated hydrochloric acid (100 ml) and the mixture was heated at 80-85° C. for 1 hour. The methanol was then distilled off and the residual aqueous solution was made basic with NaOH/H2O and extracted with ethyl acetate-tetrahydrofuran (2:1). The extract was washed with saturated NaCl/H2O and dried over MgSO4. The solvent was then distilled off under reduced pressure to provide 3-(1-acetyl-4-piperidinyl)-1-(2,3,4,5-tetrahydro-1H-2-benzazepin-8-yl)-1-propanone (4.92 g) as light-yellow oil.

Workup

  1. distillationThe methanol was then distilled off
  2. extractionextracted with ethyl acetate-tetrahydrofuran (2:1)
  3. washThe extract was washed with saturated NaCl/H2O
  4. dry with materialdried over MgSO4
  5. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-6936e19a5a0e4380a14074d662592313
Source dataset
uspto-grants-2003_03
Patent number
US06534496B1

Reaction notes

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