Triethylamine → HCID 21282944, compound

HRID 2232888Notes

Reaction equation

HRID 2232888 reaction equation
Cl.[C:2]1([CH:8]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:9][CH2:10][NH:11][CH:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=2)[CH2:13][OH:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41].C(OCC)(=O)C>O1CCOCC1>[C:44]1([CH2:43][O:42][C:40]([N:11]([CH2:10][CH2:9][CH:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=2)[CH2:13][OH:14])=[O:41])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 131715792HCID 131715792, compound

Product 1

HCID 21282944HCID 21282944, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a magnetically stirred solution of β-[(3,3-diphenylpropyl)amino]-3,4-dimethoxybenzenepropanol, monohydrochloride (3.66 mole, 1.62 g; see example 2) and triethylamine (7.32 mmole, 1.02 ml) in p-dioxane (14 ml) at room temperature under nitrogen was added benzyl chloroformate (4.39 mmole, 0.63 ml). The reaction was complete in 4 hours. The mixture was filtered and the filtrate reduced in vacuo to yield an oil. The oily residue was taken into ethyl acetate and washed with 1N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, brine, dried over magnesium sulfate, filtered and evaporated. Flash chromatography (160 g of LPS-1 silica, 1:1 ethyl acetate:hexane, eluted ~50 ml/min.) afforded 1.28 g of the title compound as an oil.

Workup

  1. filtrationThe mixture was filtered
  2. customto yield an oil
  3. washwashed with 1N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. washFlash chromatography (160 g of LPS-1 silica, 1:1 ethyl acetate:hexane, eluted ~50 ml/min.)

Sources & evidence

ORD record
ord-3cbe3ea15e4c462b95c650f601bff594
Source dataset
uspto-grants-1988_11
Patent number
US04788010

Reaction notes

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