2-Phenylpropanal → HCID 58933700, compound

HRID 854323Notes

Reaction equation

HRID 854323 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][NH:15][C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]1(C(C)C=O)C=CC=C[CH:26]=1.C([BH3-])#N.[Na+]>C(O)(=O)C.CO.[Pd]>[OH:23][C:20]1[CH:19]=[CH:18][C:17]([C:16]([NH:15][CH2:14][CH:10]2[O:11][CH2:12][CH2:13][N:8]([CH2:1][CH2:2][CH2:7][C:6]3[CH:5]=[CH:4][CH:3]=[CH:26][CH:25]=3)[CH2:9]2)=[O:24])=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 71462-PhenylpropanalHCID 5003444Sodium cyanoborohydrideHCID 58933542HCID 58933542, compound

Product 1

HCID 58933700HCID 58933700, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of N-(4-benzyl-morpholin-2-ylmethyl)-4-hydroxy-benzamide (EXAMPLE 202, Step 1) (55 mg) was dissolved in acetic acid (3 mL) and hydrogenated at 1 atm over 10% Pd/C (50 mg) for 18 h. The catalyst was removed by filtration, washed with acetic acid and the filtrate evaporated, to give an oil. A portion of this oil (21 mg) was dissolved in methanol (1 mL) and treated with phenylpropionaldehyde (24 mg) and sodium cyanoborohydride (25 mg). The resulting reaction was stirred for 15 min and the crude reaction mixture purified by preparative reverse phase IPLC to give the 4-Hydroxy-N-[4-(3-phenyl-propyl)-morpholin-2-ylmethyl]-benzamide compound.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with acetic acid
  3. customthe filtrate evaporated
  4. customto give an oil
  5. customThe resulting reaction
  6. customthe crude reaction mixture
  7. custompurified by preparative reverse phase IPLC

Sources & evidence

ORD record
ord-0f3255f8745a4829a49d26c8c66f6e15
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

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