Acetic Acid → 4-(3-Vinyl-benzyl)-morpholine

HRID 1825037Notes

Reaction equation

HRID 1825037 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)=[CH2:2].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[CH:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[CH2:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 393903-VinylbenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 221449834-(3-Vinyl-benzyl)-morpholineYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the solution of 3-vinyl benzaldehyde (5 g, 38 mmol) and morpholine (3.0 mL, 52 mmol) in dichloromethane (126 ml) was added sodium triacetoxyborohydride (19.2 g, 92 mmol) in portion at 0° C. followed by acetic acid (2.3 mL, 40 mmol). After the addition, reaction mixture was raised to room temperature and stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane washed with 1N NaOH and extracted with dichloromethane 3 times. The combined organic layer was dried over magnesium sulfate and concentrated under vacuum to give the title compound as pale yellow oil (7.2 g, 93% yield)

Workup

  1. additionAfter the addition, reaction mixture
  2. washwashed with 1N NaOH
  3. extractionextracted with dichloromethane 3 times
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ee017e977b1549cc907d6ae55a2fa0d4
Source dataset
uspto-grants-2006_05
Patent number
US07045551B2

Reaction notes

Loading…