N,N-Dimethylaniline → HCID 59134773, compound

HRID 2054452Notes

Reaction equation

HRID 2054452 reaction equation
CN(C)C1C=CC=CC=1.Cl[C:11]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)=[O:12].[Br:26][C:27]1[CH:36]=[C:35]([CH3:37])[C:34]([CH3:38])=[CH:33][C:28]=1[NH:29][CH:30]([CH3:32])[CH3:31]>C(Cl)Cl>[Br:26][C:27]1[CH:36]=[C:35]([CH3:37])[C:34]([CH3:38])=[CH:33][C:28]=1[N:29]([CH:30]([CH3:32])[CH3:31])[C:11]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)=[O:12]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 21906247HCID 21906247, compoundHCID 59655945HCID 59655945, compound

Product 1

HCID 59134773HCID 59134773, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-dimethylaniline (7.12 mL, 56.2 mmol) followed by tert-butyl 4-(chlorocarbonyl)piperidine-1-carboxylate 1-11 (42.1 mL of a 1 M solution in methylene chloride, 42.1 mmol) were added to a neat stirred mixture of 2-bromo-N-isopropyl-4,5-dimethylaniline 1-9 (6.80 g, 28.1 mmol) and N,N-dimethylamino-pyridine (172 mg, 1.40 mmol) at approximately 0° C. The resulting mixture was heated to reflux for 30 min, cooled to ambient temperature and partitioned between diethyl ether and aqueous 1 N hydrochloric acid. The organic phase was separated and washed successively with aqueous 1 N hydrochloric acid, saturated aqueous sodium bicarbonate, brine, dried (sodium sulfate) and concentrated in vacuo to give a crude residue. Purification of the crude residue by flash chromatography over silica gel (gradient elution; 0%-40% ethyl acetate/hexanes as eluent) afforded 1-12 as a white solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 30 min
  3. custompartitioned between diethyl ether and aqueous 1 N hydrochloric acid
  4. customThe organic phase was separated
  5. washwashed successively with aqueous 1 N hydrochloric acid, saturated aqueous sodium bicarbonate, brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customto give a crude residue
  9. customPurification of the crude residue by flash chromatography over silica gel (gradient elution; 0%-40% ethyl acetate/hexanes as eluent)

Sources & evidence

ORD record
ord-d82c6b69706646098d67d1c1f0e53e7f
Source dataset
uspto-grants-2008_02
Patent number
US07329673B2

Reaction notes

Loading…