Water → HCID 131732639, compound

HRID 881983Notes

Reaction equation

HRID 881983 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)[N:20]=[CH:19][N:18]=1.CCN(C(C)C)C(C)C.O>CC#N>[Cl:16][C:17]1[N:22]=[CH:21][N:20]=[C:19]([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)[N:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 178102,4-Dichloro-1,3,5-triazineHCID 81531DiisopropylethylamineHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamate

Product 1

HCID 131732639HCID 131732639, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-N-Boc-aminomethylpiperidine (25 g, 120 mmol), 2,4-Dichloro-1,3,5-Triazine (20 g, 140 mmol) and DIPEA (77.4 g, 600 mmol) in CH3CN (300 ml) was stirred at room temperature for 2 hours. Water was added and the product was extracted into ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude residue that was purified using normal phase chromatography, eluting with petroleum ether containing 30% ethyl acetate to give tert-butyl (1-(4-chloro-1,3,5-triazin-2-yl)piperidin-4-yl)methylcarbamate as an off white solid (30.0 g).

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue that was purified
  6. washeluting with petroleum ether containing 30% ethyl acetate

Sources & evidence

ORD record
ord-0637bb422d074ced9f325dc73073fb06
Source dataset
uspto-grants-2015_03
Patent number
US08993757B2

Reaction notes

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