Water → Benzyl 2-(1-aminoethyl)morpholine-4-carboxylate

HRID 1527135Notes

Reaction equation

HRID 1527135 reaction equation
[C:1]([CH:4]1[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5]1)(=O)[CH3:2].C([O-])(C)=O.[NH4+].[BH3-]C#[N:27].[Na+].O>C1COCC1.CO>[NH2:27][CH:1]([CH:4]1[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5]1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 18354411Phenylmethyl 2-acetyl-4-morpholinecarboxylate

Product 1

HCID 18354340Benzyl 2-(1-aminoethyl)morpholine-4-carboxylateYield 40%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of benzyl 2-acetylmorpholine-4-carboxylate (5.0 g, 19 mmol) in THF/MeOH (1/5, 100 mL) were added AcONH4 (14.6 g, 190 mmol) and NaBH3CN (11.8 g, 190 mmol). The mixture was stirred at room temperature for 50 hr. The mixture was concentrated to give the crude. Water (20 mL) was added and the mixture was extracted by ethyl acetate (60 mL*3). 1N HCl was added into the combined organic layers. The aqueous layer was concentrated, brought to above pH >8 with 2N NaOH and extracted by ethyl acetate (60 mL*3). The organic layer was washed with brine, dried over sodium sulfate. The mixture was concentrated to give benzyl 2-(1-aminoethyl)morpholine-4-carboxylate (2.0 g, 40%).

Workup

  1. concentrationThe mixture was concentrated
  2. customto give the crude
  3. extractionthe mixture was extracted by ethyl acetate (60 mL*3)
  4. addition1N HCl was added into the combined organic layers
  5. concentrationThe aqueous layer was concentrated
  6. extractionextracted by ethyl acetate (60 mL*3)
  7. washThe organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-10c0b5c22fcc4dd2a491eeaaeb51f853
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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