Triethylamine → HCID 58504135, compound

HRID 2407689Notes

Reaction equation

HRID 2407689 reaction equation
Cl[C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][O:10][C:6]=2[CH:5]=[N:4][N:3]=1.[NH2:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1.C(N(CC)CC)C>C(O)C.C(=O)(O)[O-].[Na+]>[C:11]1([C:8]2[C:7]3[C:2]([NH:17][CH2:18][CH:19]4[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]4)=[N:3][N:4]=[CH:5][C:6]=3[O:10][N:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 58504273HCID 58504273, compound

Product 1

HCID 58504135HCID 58504135, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

The compound prepared in Example 82 (202 mg), tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (0.266 g) and triethylamine (0.607 mL) were combined in ethanol (1.5 mL) and heated at 80° C. for 17 hours. The reaction mixture cooled to room temperature, diluted with a saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organics were dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1 to 2:1) to obtain the title compound (316 mg) having the following physical data.

Workup

  1. temperatureThe reaction mixture cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organics were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1 to 2:1)

Sources & evidence

ORD record
ord-2fa3ee1325e048f89a4be8efba24b720
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

Loading…