Acetic Acid → HCID 66775224, compound

HRID 1594188Notes

Reaction equation

HRID 1594188 reaction equation
N1C=CC=C(CNC([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23](N(CCC(O)=O)CCC2C=C(OC)C=CC=2OC)=[O:24])=O)C=1.[C:43]1([CH2:49][CH2:50][CH2:51][NH2:52])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[Na].[C:54](=[O:57])(O)[O-].[Na+].[C:59](O)(=O)C>C(OCC)(=O)C.CN(C)C=O>[CH3:54][O:57][C:23](=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:12]1[CH:11]=[CH:16][C:15]([CH2:59][NH:52][CH2:51][CH2:50][CH2:49][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:14][CH:13]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 162593-PhenylpropylamineHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 23079108HCID 23079108, compound

Product 1

HCID 66775224HCID 66775224, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound prepared in reference example 7 (1.2 g) in acetic acid (4 ml)-N,N-dimethylformamide (36 ml) were added 3-phenylpropylamine (1 g) and sodium borotriacetoxyhydride (1.6 g). The reaction mixture was stirred for 2.5 hours at room temperature. To the reaction mixture were added a saturated aqueous solution of sodium bicarbonate and ethyl acetate and extracted. The extract was washed with a saturated aqueous solution of sodium bicarbonate and anhydrous sodium sulfate and concentrated to give the title compound (1.8 g) having the following physical data.

Workup

  1. extractionextracted
  2. washThe extract was washed with a saturated aqueous solution of sodium bicarbonate and anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-99bcbcc0b1624d739376c0b982d0285c
Source dataset
uspto-grants-2007_11
Patent number
US07300917B2

Reaction notes

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