Sodium Hydroxide → 2,3-diphenylmorpholine

HRID 1381531Notes

Reaction equation

HRID 1381531 reaction equation
O[CH2:2][CH2:3][NH:4][CH:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[OH:7].[OH-].[Na+]>S(=O)(=O)(O)O>[C:8]1([CH:6]2[O:7][CH2:2][CH2:3][NH:4][CH:5]2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 234299HCID 234299, compound

Product 1

HCID 2371542,3-diphenylmorpholine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

β-[(2-Hydroxyethyl)amino]-α-phenylbenzeneethanol erythro isomer, 7.1 g (0.027 mole) was added to 20 ml of 70% sulfuric acid at 0° C. The mixture was heated at 100° C. for 3 hr and poured into ice and neutralized with 25% sodium hydroxide. The neutralized mixture was extracted with diethyl ether and the extract was dried and the solvent evaporated to give 5.8 g (54%), m.p. 70°-72° C. of solids. The solids were recrystallized from ethanol water mixture followed by low boiling petroleum ether, m.p. 82°-84° C.

Workup

  1. extractionThe neutralized mixture was extracted with diethyl ether
  2. customthe extract was dried
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-bc9c204ee3184d4592292022a4e8cbd2
Source dataset
uspto-grants-1989_02
Patent number
US04803200

Reaction notes

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