Hydrochloric Acid → HCID 69873817, compound

HRID 2306633Notes

Reaction equation

HRID 2306633 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:13][CH2:12]1)=[O:10])(C)(C)C.[ClH:33]>O1CCOCC1>[ClH:33].[C:26]1([CH2:25][C@@H:8]([NH2:7])[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])[CH2:13][CH2:12]2)=[O:10])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9803240HCID 9803240, compound

Product 1

HCID 69873817HCID 69873817, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (R)-[1-(phenylmethyl)-2-[4-(2-methoxyphenyl)-1-piperazinyl]-2-oxo-ethyl]-carbamic acid tert-butyl ester (16.37 g, 37.3 mmol) in a mixture of dioxane (150 mL)/4N aqueous HCl (150 mL) was stirred at room temperature for 6 hours. The reaction mixture was then concentrated under reduced pressure and the aqueous mixture was extracted with diethyl ether. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield the desired (R)-[1-(phenylmethyl)-2-[4-(2-methoxyphenyl)-1-piperazinyl]-2-oxoethyl]amine hydrochloride (14.0 g, 100% yield) as an off-white solid, which was used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. extractionthe aqueous mixture was extracted with diethyl ether
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f2727fefe76b42d5bc45f37f55feb636
Source dataset
uspto-grants-2004_12
Patent number
US06828324B2

Reaction notes

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