Benzoyl chloride → HCID 68915164, compound

HRID 732727Notes

Reaction equation

HRID 732727 reaction equation
[C:1]1([C@H:11]([N:13]([CH2:21][CH:22]2[CH2:26][CH2:25][NH:24][CH2:23]2)C(=O)OC(C)(C)C)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:27]([Cl:35])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)(O)[O-].[Na+]>C1COCC1>[ClH:35].[C:27]([N:24]1[CH2:25][CH2:26][CH:22]([CH2:21][NH:13][C@@H:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[CH3:12])[CH2:23]1)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 86628568HCID 86628568, compound

Product 1

HCID 68915164HCID 68915164, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 8.0 ml THF solution of 124 mg of tert-butyl [(1R)-1-(1-naphthyl)ethyl](pyrrolidin-3-ylmethyl)carbamate was mixed with 45 μl of benzoyl chloride and stirred overnight at room temperature. A 20 ml portion of saturated sodium bicarbonate aqueous solution was added thereto, and the solvent was evaporated. This was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate, and the solvent was evaporated. The thus obtained residue was treated with 4 M hydrogen chloride/ethyl acetate and recrystallized from isopropanol-diethyl ether to obtain 100 mg of (1R)—N-[(1-benzoylpyrrolidin-3-yl)methyl]-1-(1-naphthyl)ethanamine hydrochloride as colorless crystals.

Workup

  1. customthe solvent was evaporated
  2. extractionThis was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customthe solvent was evaporated
  6. additionThe thus obtained residue was treated with 4 M hydrogen chloride/ethyl acetate
  7. customrecrystallized from isopropanol-diethyl ether

Sources & evidence

ORD record
ord-aa9c3866ff5a442e94bbe714badea894
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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