Phenylacetyl chloride → HCID 18433031, compound

HRID 2305545Notes

Reaction equation

HRID 2305545 reaction equation
[NH2:1][CH2:2][CH:3]([OH:22])[CH2:4][NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:7]=1.C(N(CC)CC)C.[C:30]1([CH2:36][C:37]([Cl:39])=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.Cl.CCOCC>O1CCOCC1.CO>[ClH:39].[OH:22][CH:3]([CH2:4][NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:7]=1)[CH2:2][NH:1][C:37](=[O:38])[CH2:36][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 10953452Ether hydrochlorideHCID 18432975HCID 18432975, compound

Product 1

HCID 18433031HCID 18433031, compoundYield 25.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a room temperature solution of (RS)-1-amino-3-(2-phenyl-quinolin-4-ylamino)-propan-2-ol (0.293 g, 1 mmol) and triethylamine (0.42 ml,3 mmol) in dioxane (6 ml) was added a solution of phenylacetylchloride (0.198 ml, 1.5 mmol) in dioxane (1 ml). After stirring for 3 hours at room temperature, the reaction mixture was quenched with H2O and 1N NaOH. The aqueous phase was extracted with CH2Cl2 (5×10 ml). The combined organic phases were dried over Na2SO4, concentrated and chromatographed over silica gel (CH2Cl2—MeOH, 19:1 then 9:1) to provide a yellow oil which was dissolved in MeOH. HCl-Et2O was added to provide (RS)-N-[2-hydroxy-3-(2-phenyl-quinolin-4-ylamino)-propyl]-2-phenyl-acetamide hydrochloride (0.113 g, 25%) as a light yellow foam, MS: m/e=412.3 (M+H+).

Workup

  1. customthe reaction mixture was quenched with H2O and 1N NaOH
  2. extractionThe aqueous phase was extracted with CH2Cl2 (5×10 ml)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated
  5. customchromatographed over silica gel (CH2Cl2—MeOH, 19:1
  6. custom9:1) to provide a yellow oil which

Sources & evidence

ORD record
ord-0a0f009f4af2466c8696d99889da230c
Source dataset
uspto-grants-2002_08
Patent number
US06440995B1

Reaction notes

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