Methylamine → Ethyl 1-[4-chloro-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylate

HRID 1678442Notes

Reaction equation

HRID 1678442 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)[N:3]=1.CN.[CH:22]([N:25](C(C)C)CC)(C)C>ClCCl>[Cl:8][C:6]1[N:7]=[C:2]([NH:25][CH3:22])[N:3]=[C:4]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)[N:5]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 2774159Ethyl 1-(4,6-dichloro-1,3,5-triazin-2-yl)piperidine-4-carboxylate

Product 1

HCID 86644318Ethyl 1-[4-chloro-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 1-(4,6-dichloro-1,3,5-triazin-2-yl)-4-piperidinecarboxylate (1.0 g, 3.3 mmol, 1.0 equiv) in dichloromethane (20 ml) at room temperature, a premixed solution of methylamine (1.6 ml, 3.3 mmol, 1.0 equiv) and diisopropylethylamine (DIEA, 1.7 ml, 9.8 mmol, 3.0 equiv) in dichloromethane (10 ml) was added dropwise. The reaction was stirred for 3 h at room temperature. The solvent was removed under reduced pressure to afford 983 mg (100%) of the title compound. MS (ES+): m/e 300.1 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-18b04e3fc22848c891c188fbedc7753e
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

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