Phenethylamine → HCID 11439260, compound

HRID 2119326Notes

Reaction equation

HRID 2119326 reaction equation
[CH2:1](CN)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:11]1[CH:12]=[C:13]([CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.[C:27](#[N:29])C>>[CH2:1]([N:29]([CH3:27])[C:11]1[CH:12]=[C:13]([CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 1001PhenethylamineHCID 6342AcetonitrileHCID 112764954-(3-FLUORO-4-NITROBENZYL)MORPHOLINE

Product 1

HCID 11439260HCID 11439260, compound

Procedure

A mixture of N-benzylmethylamine (3.6 g, 30 mmol) and 4-(3-fluoro-4-nitrobenzyl)morpholine (2.4 g, 10 mmol) in acetonitrile (3.0 mL) is heated under reflux for 30 min and the solvent is then removed under reduced pressure. The residual oil is partitioned between ethyl acetate (70 mL) and sodium hydroxide solution (10 mL of 1 N) and the ethyl acetate phase is separated and washed twice with water (5 mL). The ethyl acetate is removed and the crude product is applied to a silica gel column. The column is eluted with 50% ethyl acetate/hexane to give 3.3 g of the title compound as an oil.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 30 min
  3. customthe solvent is then removed under reduced pressure
  4. customThe residual oil is partitioned between ethyl acetate (70 mL) and sodium hydroxide solution (10 mL of 1 N)
  5. customthe ethyl acetate phase is separated
  6. washwashed twice with water (5 mL)
  7. customThe ethyl acetate is removed
  8. washThe column is eluted with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-7d7775bb55244c68b9f2dadc6616b491
Source dataset
uspto-grants-2004_02
Patent number
US06686356B2

Reaction notes

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