Sodium hydride → 2-Phenyl-2,3,4,5-tetrahydro-[6H]-1,5-benzoxazocine

HRID 2058656Notes

Reaction equation

HRID 2058656 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][CH2:10][CH2:11][CH:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+]>CS(C)=O>[C:13]1([CH:12]2[CH2:11][CH2:10][NH:9][CH2:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[O:19]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 12951841N-(2-Fluorophenylmethyl)-3-hydroxy-3-phenylpropylamine

Product 1

HCID 129518422-Phenyl-2,3,4,5-tetrahydro-[6H]-1,5-benzoxazocineYield 40.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-(2-fluorophenylmethyl)-3-hydroxy-3-phenylpropylamine (4.5 g, 17 mM), 50% sodium hydride dispersion (870 mg, 17 mM) and dimethylsulphoxide (200 ml) was stirred for 24 hours at 50° C. under argon. The mixture was cooled to ambient temperature, poured onto water (700 ml) and extracted with ether (3×200 ml). The combined ether layers were extracted with 1 N hydrochloric acid (3×50 ml), the acid layer basified and extracted with ether (2×200 ml). The organic phase was dried and the solvent removed under reduced pressure. Recrystallisation from cyclohexane gave the title compound (1.7 g) m.p. 73°-4° C. Found: C, 80.1; H, 7.4; N, 5.9%; C16H17NO requires: C, 80.3; H, 7.2; N, 5.9%.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. additionpoured onto water (700 ml)
  3. extractionextracted with ether (3×200 ml)
  4. extractionThe combined ether layers were extracted with 1 N hydrochloric acid (3×50 ml)
  5. extractionextracted with ether (2×200 ml)
  6. customThe organic phase was dried
  7. customthe solvent removed under reduced pressure
  8. customRecrystallisation from cyclohexane

Sources & evidence

ORD record
ord-19953b98ecc044b6b6291e5482054bcd
Source dataset
uspto-grants-1982_03
Patent number
US04318909

Reaction notes

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