Sodium Hydroxide → HCID 22674567, compound

HRID 1006331Notes

Reaction equation

HRID 1006331 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([N-][C@@H:15]1[CH2:20][O:19][CH2:18][C:17](=O)[N:16]1[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)C1C=CC=CC=1.[OH-].[Na+]>O1CCCC1>[CH2:22]([NH:16][CH2:15][CH:17]1[CH2:18][O:19][CH2:20][CH2:15][N:16]1[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86589634HCID 86589634, compound

Product 1

HCID 22674567HCID 22674567, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Lithium aluminum hydride (4.7 g) was added by small portions to a solution of N-benzyl((3S)-4-benzyl-5-oxomorpholin-3-yl)amide (8.0 g) in tetrahydrofuran (50 ml) under nitrogen atmosphere, and the whole was stirred at 70° C. for 15 hours. After being cooled with ice, 2N sodium hydroxide (2 ml) was added to the mixture under nitrogen atmosphere. The resulting precipitates were filtered off and washed with tetrahydrofuran, and the filtrate and the washings were combined and evaporated under reduced pressure to give a crude oil. The oil was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (9:1). The fractions containing the objective compound were collected, evaporated under reduced pressure to give an oil of N-benzyl[(4-benzylmorpholin-3-yl)methyl]amine (2.4 g).

Workup

  1. additionwas added to the mixture under nitrogen atmosphere
  2. customThe resulting precipitates
  3. filtrationwere filtered off
  4. washwashed with tetrahydrofuran
  5. customevaporated under reduced pressure
  6. customto give a crude oil
  7. customThe oil was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (9:1)
  8. additionThe fractions containing the objective compound
  9. customwere collected
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5b5cb2b465da4c04b7b4ef014c6e4897
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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