Triethylamine → HCID 58878512, compound

HRID 1441658Notes

Reaction equation

HRID 1441658 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=1[NH2:30].C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:16])[NH:30][C:23]2[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:22]=2[Br:21])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 7930162-Bromo-5-methoxyaniline

Product 1

HCID 58878512HCID 58878512, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

Piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (2.9 g, 12.68 mmol) was dissolved in dry methylene chloride (19 mL) and dry pyridine (2.61 mL). To the reaction mixture was then added thionyl chloride (1.81 g, 15.22 mmol) under nitrogen atmosphere and the reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture was then added successively, under nitrogen atmosphere, 2-bromo-5-methoxy-phenylamine (2.82 g, 13.95 mmol), dry triethylamine (4.49 g, 44.40 mmol), dry methylene chloride (23 mL), 4-(dimethylamino)pyridine (0.15 g, 1.26 mmol) and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was then partitioned with aqueous 2N HCl and tert-butyl methyl ether. The organic layer was washed with aqueous 2N HCl, aqueous NaHCO3, brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (25% ethyl acetate/hexanes) to yield the title compound as a solid.

Workup

  1. additionTo the reaction mixture was then added successively, under nitrogen atmosphere
  2. customThe reaction mixture was then partitioned with aqueous 2N HCl and tert-butyl methyl ether
  3. washThe organic layer was washed with aqueous 2N HCl, aqueous NaHCO3, brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. customto yield a crude oil
  8. customThe crude oil was purified via flash chromatography (25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ca1752e050ec4f318ecd870c6a883bc6
Source dataset
uspto-grants-2010_02
Patent number
US07655670B2

Reaction notes

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