Benzene → HCID 22998310, compound

HRID 1420646Notes

Reaction equation

HRID 1420646 reaction equation
[NH2-].[Na+].[CH3:3][N:4]([CH3:20])[C:5]1[CH:6]=[CH:7][C:8]2[CH2:14][CH2:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[NH:10][C:9]=2[CH:19]=1.[OH2:21].[CH:22]1[CH:27]=CC=C[CH:23]=1>C(Cl)(Cl)Cl>[CH3:3][N:4]([CH3:20])[C:5]1[CH:6]=[CH:7][C:8]2[CH2:14][CH2:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[N:10]([CH2:23][CH2:22][CH2:27][OH:21])[C:9]=2[CH:19]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 962WaterHCID 24533Sodium amideHCID 22998297HCID 22998297, compound

Product 1

HCID 22998310HCID 22998310, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of sodium amide (2.6 g, 0.033 mol, 50% wt suspension in toluene) was added to a solution of 3-dimethylamino-10,11-dihydro-5H-dibenz[b,f]azepine (6.1 g, 0,0256 mol, prepared similarly as described in Brit. Pat., 1040739,1966) in dry benzene (60 ml). The reaction mixture was heated to 70° C. for 1 h. 3-Bromo-1-propyl-tetrahydro-2-pyranyl ether (7.35 g, 0.033 mol) was added and the mixture was heated at reflux temperature for 20 h. To the cooled reaction mixture, water (20 ml) was added, and the phases were separated. The solvent was evaporated from the organic phase and the residue was dissolved in a mixture of methanol (100 ml) and 5 N HCl (30 ml). The mixture was heated at reflux temperature for 15 minutes, and methanol was evaporated. Water (50 ml) was added, pH was adjusted to 8-9 with aqueous ammonia and the mixture was extracted with benzene (2×150 ml). The combined organic extracts were dried (K2CO3), filtered and the solvent was evaporated under vacuum. The residue, was purified by chromatography on silica gel (50 g) using first benzene as eluent to isolate the starting material. Then, using chloroform as eluent, 3.5 g of 3-(3-di-methylamino-10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propanol as an oil was isolated.

Workup

  1. customprepared similarly
  2. temperaturethe mixture was heated
  3. temperatureat reflux temperature for 20 h
  4. additionwas added
  5. customthe phases were separated
  6. customThe solvent was evaporated from the organic phase
  7. dissolutionthe residue was dissolved in a mixture of methanol (100 ml) and 5 N HCl (30 ml)
  8. temperatureThe mixture was heated
  9. temperatureat reflux temperature for 15 minutes
  10. custommethanol was evaporated
  11. additionWater (50 ml) was added
  12. extractionthe mixture was extracted with benzene (2×150 ml)
  13. dry with materialThe combined organic extracts were dried (K2CO3)
  14. filtrationfiltered
  15. customthe solvent was evaporated under vacuum
  16. customThe residue, was purified by chromatography on silica gel (50 g)
  17. customto isolate the starting material

Sources & evidence

ORD record
ord-da551a33fe3949d4a728d700ad7920ad
Source dataset
uspto-grants-2000_06
Patent number
US06071901

Reaction notes

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