Cyanuric chloride → Ethyl 1-(4,6-dichloro-1,3,5-triazin-2-yl)piperidine-4-carboxylate

HRID 1678441Notes

Reaction equation

HRID 1678441 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([Cl:9])[N:3]=1.[NH:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]1.C(N(C(C)C)CC)(C)C>ClCCl>[Cl:9][C:4]1[N:5]=[C:6]([Cl:8])[N:7]=[C:2]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]2)[N:3]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 70770Ethyl 4-piperidinecarboxylateHCID 81531Diisopropylethylamine

Product 1

HCID 2774159Ethyl 1-(4,6-dichloro-1,3,5-triazin-2-yl)piperidine-4-carboxylateYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2,4,6-trichloro-1,3,5-triazine (5.0 g, 27 mmol, 1.0 equiv) in dichloromethane (50 ml) at −50° C., a premixed solution of ethyl 4-piperidinecarboxylate (4.1 ml, 27 mmol, 1.0 equiv) and diisopropylethylamine (DIEA, 14.2 ml, 81.3 mmol, 3.00 equiv) in dichloromethane (100 ml) was added dropwise via an addition funnel. The reaction mixture was allowed to warm to room temperature, and stirring was continued overnight. The solvent was removed under reduced pressure to yield 7.95 g (96%) of the title compound. MS (ES+): m/e 305.3 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d7adca99942f42daa8af982235e142e3
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

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