Ethyl 4-piperidinecarboxylate → HCID 86690734, compound

HRID 1473916Notes

Reaction equation

HRID 1473916 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[C:17]2[CH2:16][O:15][C:14]([CH3:19])([CH3:18])[O:13][C:12]=2[CH:11]=[CH:10][CH:9]=1)(=O)=O.[NH:20]1[CH2:25][CH2:24][CH:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]1>CN(C=O)C>[CH3:18][C:14]1([CH3:19])[O:13][C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([CH2:7][CH2:6][N:20]3[CH2:25][CH2:24][CH:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]3)[C:17]=2[CH2:16][O:15]1

Participants

4

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 86690733HCID 86690733, compound

Product 1

HCID 86690734HCID 86690734, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 2-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-5-yl)ethyl methanesulfonate (176 mg, 0.59 mmol, crude above, 1 eq.) in DMF (1.0 mL) was added ethyl piperidine-4-carboxylate (186 mg, 1.18 mmol, 2.0 eq.) at rt. The mixture was stirred at 60° C. for 2 h, cooled to rt, and purified on RP-HPLC (Gemini 21.2 mm×150 mm) using a mixture of CH3CN and water (0.1% HCOOH) as eluent to give ethyl 1-(2-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-5-yl)ethyl)piperidine-4-carboxylate (100 mg, 49% for two steps). 1H NMR (400 MHz, CDCl3) δ 8.45 (s, 1H), 7.13 (t, J=7.9 Hz, 1H), 6.73 (d, J=7.9 Hz, 2H), 4.86 (s, 2H), 4.19 (q, J=7.1 Hz, 2H), 3.22 (s, 2H), 3.09-2.95 (m, 1H), 2.95-2.79 (m, 4H), 2.76 (s, 1H), 2.66-2.48 (m, 1H), 2.23-1.99 (m, 4H), 1.55 (s, 6H), 1.29 (t, J=7.1 Hz, 3H). LRMS (M+H+) m/z 348.1.

Workup

  1. temperaturecooled to rt
  2. custompurified on RP-HPLC (Gemini 21.2 mm×150 mm)
  3. additiona mixture of CH3CN and water (0.1% HCOOH) as eluent

Sources & evidence

ORD record
ord-31c16fa31b4f4ef6b41bc580770d52d2
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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