Morpholine → 4-[(4-Bromothien-2-YL)methyl]morpholine

HRID 361357Notes

Reaction equation

HRID 361357 reaction equation
C([BH3-])#N.[Na+].[Br:5][C:6]1[CH:7]=[C:8]([CH:11]=O)[S:9][CH:10]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(=O)(O)[O-].[Na+]>C(O)C.C(O)(=O)C>[Br:5][C:6]1[CH:7]=[C:8]([CH2:11][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[S:9][CH:10]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 877924-Bromothiophene-2-carbaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 7834974-[(4-Bromothien-2-YL)methyl]morpholineYield 50.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

Sodium cyanoborohydride (2 g) was added portionwise to a stirred mixture of 4-bromo-2-thiophenecarbaldehyde (4.78 g), morpholine (2.1 g), glacial acetic acid (1.8 g) and ethanol (125 ml). The mixture was stirred at ambient temperature for 1 hour. The mixture was poured into a saturated aqueous sodium bicarbonate solution and extracted with methylene chloride. The organic phase was washed with brine and evaporated. The resultant oil was partitioned between a dilute (10%) aqueous hydrochloric acid solution and methylene chloride. The aqueous phase was basified by the addition of a saturated aqueous sodium bicarbonate solution and extracted with methylene chloride. The organic extract was dried (MgSO4) and evaporated to give 4-bromo-2-morpholinomethylthiophene (3.2 g);

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic phase was washed with brine
  3. customevaporated
  4. customThe resultant oil was partitioned between
  5. additiona dilute (10%) aqueous hydrochloric acid solution and methylene chloride
  6. additionThe aqueous phase was basified by the addition of a saturated aqueous sodium bicarbonate solution
  7. extractionextracted with methylene chloride
  8. extractionThe organic extract
  9. dry with materialwas dried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-a14cb0c8039c46fc939b661a2cbf9c76
Source dataset
uspto-grants-1999_02
Patent number
US05866572

Reaction notes

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