Acetone → (Phenylmethyl) [5-[2-[4-(4-morpholinyl)phenyl]ethoxy] pentyl]carbamate

HRID 2166164Notes

Reaction equation

HRID 2166164 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].C[C:8](C)([CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1)C(O)=O.C(N([CH2:37][CH3:38])CC)C.[N-:39]=[N+]=[N-].[Na+].[CH3:43][C:44]([CH3:46])=O>O>[N:25]1([C:22]2[CH:21]=[CH:20][C:19]([CH2:18][CH2:17][O:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:8][NH:39][C:2](=[O:3])[O:4][CH2:5][C:6]3[CH:38]=[CH:37][CH:46]=[CH:44][CH:43]=3)=[CH:24][CH:23]=2)[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1

Participants

7

Reactant 5

HCID 180Acetone2×HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 200628192,2-Dimethyl-6-[2-[4-(4-morpholinyl)phenyl]ethoxy]hexanoic acid

Product 1

HCID 53892071(Phenylmethyl) [5-[2-[4-(4-morpholinyl)phenyl]ethoxy] pentyl]carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

Ethyl chloroformate (3.29 g) in acetone (10 ml) was added dropwise to a solution of the product of stage (iii) (10.0 g) and triethylamine (3.0 g, 30 mmol) in acetone (100 ml) and water (10 ml) at 0°. The mixture was stirred at 0° for 40 min and sodium azide (2.0 g) in water (25 ml) was added dropwise. The resulting suspension was stirred at room temperature for 45 min, diluted with water (200 ml) and extracted with T (2×200 ml). The dried (Na2SO4) extract was heated at 75°-80° for 2.5 h and evaporated. The residue was treated with benzyl alcohol (20 ml), heated at 75°-80° for 60 h and benzyl alcohol was removed by distillation (~1 mmHg). The resulting oil was purified on a column of silica (Merck 9385) eluted with ER-CX (1:2) to give the title compound, as a yellow oil (4.74 g). T.l.c. ER-CX (1:2) Rf 0.13.

Workup

  1. stirringThe resulting suspension was stirred at room temperature for 45 min
  2. extractionextracted with T (2×200 ml)
  3. dry with materialThe dried (Na2SO4)
  4. extractionextract
  5. temperaturewas heated at 75°-80° for 2.5 h
  6. customevaporated
  7. additionThe residue was treated with benzyl alcohol (20 ml)
  8. temperatureheated at 75°-80° for 60 h
  9. custombenzyl alcohol was removed by distillation (~1 mmHg)
  10. customThe resulting oil was purified on a column of silica (Merck 9385)
  11. washeluted with ER-CX (1:2)

Sources & evidence

ORD record
ord-89c3f088cd774184ba4f1c7e1fff7f2c
Source dataset
uspto-grants-1990_07
Patent number
US04943591

Reaction notes

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