Ammonia → n-(3-Oxopropyl)-n-phenethyl-3-phenethyloxy-propanamide

HRID 2234178Notes

Reaction equation

HRID 2234178 reaction equation
C([O:3][CH:4](OCC)[CH2:5][CH2:6][N:7]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8](=[O:20])[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)C.Cl.Cl.NCCC1C2SC(=O)NC=2C(O)=CC=1.C([BH3-])#N.[Na+].N>O1CCOCC1.CO.O.C(O)(=O)C.ClCCl>[O:3]=[CH:4][CH2:5][CH2:6][N:7]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8](=[O:20])[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

11

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 602075534-Hydroxy-7-(2-aminoethyl)-1,3-benzothiazol-2(3H)-one hydrochlorideHCID 68701548N-(3,3-Diethoxypropyl)-N-phenethyl-3-phenethyloxy-propanamide

Product 1

HCID 86258469n-(3-Oxopropyl)-n-phenethyl-3-phenethyloxy-propanamide

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of N-(3,3-diethoxypropyl)-N-phenethyl-3-phenethyloxy-propanamide (Example 8b), 0.127 g) in dioxane (10 mL) was treated with concentrated hydrochloric acid (1 mL) and stirred at room temperature for 30 minutes. After this time the solution was diluted (dichloromethane 30 mL), washed with water (2×20 mL), brine (20 mL), dried over magnesium sulfate and concentrated to give the crude aldehyde product (0.13 g) which was used immediately. The crude aldehyde was dissolved in methanol (20 mL) and 7-(2-aminoethyl)-4-hydroxy-3H-benzothiazol-2-one hydrochloride (0.078 g) was added along with acetic acid (0.1 mL) and water (0.1 mL). After stirring at room temperature for 30 minutes, sodium cyanoborohydride (0.012 g) was added and the reaction mixture stirred overnight. Ammonia (7N in methanol, 1 mL) was added and the mixture was concentrated. The resulting residue was taken up in ethyl acetate (50 mL), washed with water (2×20 mL), brine (20 mL), dried over magnesium sulfate and concentrated to give the crude product which was purified by flash column chromatography eluting with 1% ammonia; 5% methanol in dichloromethane to afford the titled compound as a white solid (0.078 g).

Workup

  1. washwashed with water (2×20 mL), brine (20 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customto give the crude aldehyde product (0.13 g) which
  5. stirringAfter stirring at room temperature for 30 minutes
  6. stirringthe reaction mixture stirred overnight
  7. concentrationthe mixture was concentrated
  8. washwashed with water (2×20 mL), brine (20 mL)
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customto give the crude product which
  12. customwas purified by flash column chromatography
  13. washeluting with 1% ammonia

Sources & evidence

ORD record
ord-35be81b6fb14486eac53d0489883b7b6
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

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