Triethylamine → 4-(7-Fluoro-3-methoxycarbonylmethyl-2-methyl-naphthalene-1-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1929578Notes

Reaction equation

HRID 1929578 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16](Cl)=[O:17])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:19])[CH:11]=2)[CH:6]=1.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].C(N(CC)CC)C>ClCCl>[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:16]([C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([F:19])[CH:11]=3)[CH:6]=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:20])[C:14]=2[CH3:15])=[O:17])[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 59326710(4-Chlorocarbonyl-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl ester

Product 1

HCID 593267254-(7-Fluoro-3-methoxycarbonylmethyl-2-methyl-naphthalene-1-carbonyl)-piperazine-1-carboxylic acid tert-butyl esterYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-chlorocarbonyl-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl ester (294 mg, 1.0 mmol) and piperazine-1-carboxylic acid tert-butyl ester (279 mg, 1.5 mmol) in dichloromethane was added triethylamine (458 μL, 3.3 mmol). The resulting mixture was stirred at room temperature overnight, and concentrated in vacuo. The residue was purified by column chromatography (gradient elution with 20-40% ethyl acetate in petroleum ether) to afford 4-(7-fluoro-3-methoxycarbonylmethyl-2-methyl-naphthalene-1-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester (410 mg, 92%) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (gradient elution with 20-40% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-d95064743bd849e8824961e2df5d96fd
Source dataset
uspto-grants-2012_05
Patent number
US08188090B2

Reaction notes

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