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

HRID 979344Notes

Reaction equation

HRID 979344 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-0d19683d5d7343748d2327e009e6e47f
Source dataset
uspto-grants-1987_05
Patent number
US04667039

Reaction notes

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