Triethylamine → HCID 23396321, compound

HRID 881977Notes

Reaction equation

HRID 881977 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])[CH3:3].[Cl:16][C:17]1[N:22]=[C:21](Cl)[CH:20]=[CH:19][N:18]=1.C(N(CC)CC)C>C(O)C.C(Cl)Cl>[Cl:16][C:17]1[N:22]=[C:21]([N:13]2[CH2:12][CH2:11][CH:10]([CH2:9][NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:15][CH2:14]2)[CH:20]=[CH:19][N:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamate

Product 1

HCID 23396321HCID 23396321, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-N-Boc-aminomethylpiperidine (4.95 g, 23.1 mmol), 2,4-dichloropyrimidine (3.28 g, 22.0 mmol) and triethyl amine (7.84 g, 77.5 mmol) in ethanol (90 ml) was stirred at 85° C. for 45 minutes. The reaction mixture was concentrated under reduced pressure and the residue obtained was dissolved in CH2Cl2 and filtered. The solvent was removed under reduced pressure to give a crude residue that was purified using normal phase chromatography, eluting with iso-hexane and increasing amounts of ethyl acetate to give tert-butyl (1-(2-chloropyrimidin-4-yl)piperidin-4-yl)methylcarbamate as an off white solid (6.0 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue obtained
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure
  5. customto give a crude residue that
  6. customwas purified
  7. washeluting with iso-hexane
  8. temperatureincreasing amounts of ethyl acetate

Sources & evidence

ORD record
ord-dc1eda5f00c8422aa07308700e187618
Source dataset
uspto-grants-2015_03
Patent number
US08993757B2

Reaction notes

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