Sodium Bicarbonate → 11-{1-[2-(4-Hydroxy-3-methoxyphenyl)ethyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine

HRID 2119011Notes

Reaction equation

HRID 2119011 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH:7]2[C:13]3=[CH:14][CH:15]=[CH:16][N:12]3[CH2:11][C:10]3[CH:17]=[CH:18][CH:19]=[CH:20][C:9]=3[O:8]2)[CH2:3][CH2:2]1.[OH:21][C:22]1[CH:30]=[CH:29][C:25]([CH2:26][CH2:27]Cl)=[CH:24][C:23]=1[O:31][CH3:32].C([O-])(O)=O.[Na+]>C(OCCCC)(=O)C>[OH:21][C:22]1[CH:30]=[CH:29][C:25]([CH2:26][CH2:27][N:1]2[CH2:2][CH2:3][CH:4]([CH:7]3[C:13]4=[CH:14][CH:15]=[CH:16][N:12]4[CH2:11][C:10]4[CH:17]=[CH:18][CH:19]=[CH:20][C:9]=4[O:8]3)[CH2:5][CH2:6]2)=[CH:24][C:23]=1[O:31][CH3:32]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 1368935811-(piperdin-4-yl)-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepineHCID 212240924-Hydroxy-3-methoxyphenethyl chloride

Product 1

HCID 1368940611-{1-[2-(4-Hydroxy-3-methoxyphenyl)ethyl]piperidin-4-yl}-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine

Reagents, catalysts & solvents 1

HCID 31272Butyl AcetateSolvent

Procedure

A mixture of 11-(piperidin-4-yl)-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine (5.1 g, 0.019 mole), 4-hydroxy-3-methoxyphenethyl chloride (4.25 g, 0.023 mole) and NaHCO3 (11 g) in 110 ml n-butyl acetate was heated at reflux for 18 hours. The reaction mixture was then cooled, filtered and concentrated to an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe reaction mixture was then cooled
  4. filtrationfiltered
  5. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-ba59cb15c6e445bfac647babcccd830c
Source dataset
uspto-grants-1987_07
Patent number
US04681879

Reaction notes

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