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

HRID 365153

Reaction equation

HRID 365153 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-a3b0754bd19445228a2e164f35fe5127
Source dataset
uspto-grants-1986_08
Patent number
US04608374

Linked notes

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