Water → dimethyl{[(3R)-4-(phenylmethyl)-3-morpholinyl]methyl}amine

HRID 1366540Notes

Reaction equation

[CH3:1][N:2]([CH3:19])[C:3]([C@@H:5]1[CH2:10][O:9][CH2:8][C:7](=O)[N:6]1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH3:1][N:2]([CH3:19])[CH2:3][C@@H:5]1[CH2:10][O:9][CH2:8][CH2:7][N:6]1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(3S)—N,N-Dimethyl-5-oxo-4-(phenylmethyl)-3 morpholinecarboxamide (390 mg, 1.5 mmol) was dissolved in THF (20 mL) and the solution was cooled to 0° C. LiAlH4 (225 mg, 5.9 mmol) was added and the resulting mixture was refluxed overnight. Upon cooling to 0° C., water (1.4 mL) was added followed by 15% (w/w) NaOH (aq) (1.4 mL) and finally another portion of water (4.2 mL). Stirring for 30 min followed by filtration and concentration in vacuo yielded a crude mixture which was purified by RP-HPLC to provide dimethyl{[(3R)-4-(phenylmethyl)-3-morpholinyl]methyl}amine (510 mg, 41%). LCMS: (M+H)+: 235.2.

Workup

temperaturethe resulting mixture was refluxed overnight
temperatureUpon cooling to 0° C.
filtrationfollowed by filtration and concentration in vacuo
customyielded a crude mixture which
customwas purified by RP-HPLC

Sources & evidence

ORD record: ord-4af5e2a97d0b43f284dc6aa3f57ca16d
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893056B2

Reaction notes

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