Triethylamine → 1-Benzyl-4-[N-ethyl-N-(6-chloro-5-nitro-4-pyrimidinyl)amino]piperidine

HRID 361864

Reaction equation

HRID 361864 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[CH2:19]([N:26]1[CH2:31][CH2:30][CH:29]([N:32](CC)[C:33]2[C:38](NCC)=CC=CN=2)[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:19]([N:26]1[CH2:31][CH2:30][CH:29]([N:32]([CH2:33][CH3:38])[C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=2)[CH2:28][CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 203124,6-Dichloro-5-nitropyrimidineHCID 516892Sodium BicarbonateHCID 104972481-Benzyl-4-[N-ethyl-N-(3-(ethylamino)-2-pyridinyl)amino]piperidine

Product 1

HCID 544731551-Benzyl-4-[N-ethyl-N-(6-chloro-5-nitro-4-pyrimidinyl)amino]piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4,6-Dichloro-5-nitropyrimidine (8.88 g) is dissolved in 400 ml of methylene chloride and cooled to -78°. Then triethylamine (6.7 ml) and 1-benzyl-4-N-ethylaminopiperidine (EXAMPLE 205, 10.00 g) is added and the reaction is stirred 1 hr at -78° and slowly warmed to 20°-25°. The reaction is poured into saturated aqueous sodium bicarbonate, extracted with methylene chloride, washed with saline, dried and concentrated under reduced pressure. Purification by flash column chromatography (10% ethyl acetate/hexane to 50% ethyl acetate/hexane) gives the title compound.

Workup

  1. temperaturecooled to -78°
  2. temperatureslowly warmed to 20°-25°
  3. extractionextracted with methylene chloride
  4. washwashed with saline
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography (10% ethyl acetate/hexane to 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4edf6c954f5d40a1a38d8709acd6c1fe
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Linked notes

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