Triethylamine → N-(3-piperidin-1-yl-propyl)-terephthalamic acid methyl ester

HRID 1676949Notes

Reaction equation

HRID 1676949 reaction equation
C(N(CC)CC)C.[N:8]1([CH2:14][CH2:15][CH2:16][NH2:17])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[Cl-].[CH3:19][O:20][C:21](=[O:31])[C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1>C(Cl)Cl>[CH3:19][O:20][C:21](=[O:31])[C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:17][CH2:16][CH2:15][CH2:14][N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:27])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 19049Piperidine-1-propylamineHCID 53442854Terephthalic acid monomethylester chloride

Product 1

HCID 11673899N-(3-piperidin-1-yl-propyl)-terephthalamic acid methyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Triethylamine (250 mg, 2.5 mmol) and 3-piperidinopropylamine (284 mg, 2.0 mmol) are dissolved in CH2Cl2 (5 mL). Terephtalic acid monomethyl ester chloride (197 mg, 2.0 mmol) in 2.0 ml of CH2Cl2 is added to the mixture. The reaction mixture is stirred at room temperature for 2 h. The reaction is diluted with CH2Cl2 and washed with brine. The separated organic layer is dried over Na2SO4 and evaporated. The crude material is purified by silica-gel column chromatography (CH2Cl2:2M NH3 in MeOH) to give 473 mg (78%) of the title compound. MS (APCI+) 305 (M+H)+.

Workup

  1. washwashed with brine
  2. dry with materialThe separated organic layer is dried over Na2SO4
  3. customevaporated
  4. customThe crude material is purified by silica-gel column chromatography (CH2Cl2:2M NH3 in MeOH)

Sources & evidence

ORD record
ord-0a3e8aa707ac4276be9676d9852195ce
Source dataset
uspto-grants-2011_08
Patent number
US08008296B2

Reaction notes

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