Benzylamine → HCID 66811489, compound

HRID 1099197Notes

Reaction equation

HRID 1099197 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]1[C:20](O)=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>CN(C=O)C.CCOC(C)=O>[CH2:23]([NH:30][C:20]([CH:9]1[CH:10]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:11][CH2:12][CH2:13][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 5

HCID 7504BenzylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 450739411-(tert-Butoxycarbonyl)-3-phenylpiperidine-2-carboxylic acid

Product 1

HCID 66811489HCID 66811489, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-3-phenylpiperidine-2-carboxylic acid (1.03 g, 3.36 mmol) in DMF (5 ml) were added benzyl amine (0.4 ml, 3.70 mmol), 1-hydroxybenzotriazole (567 mg, 3.70 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (949 mg, 4.70 mmol). The reaction was adjusted to pH 7 with the addition of diisopropylethylamine and allowed to stir for 1 h. The reaction mixture was diluted with EtOAc, washed with saturated sodium bicarbonate (3×) and brine (2×), dried over sodium sulfate, filtered, and concentrated in vacuo to yield tert-butyl 2-[(benzylamino)carbonyl]-3-phenylpiperidine-1-carboxylate (100%).

Workup

  1. washwashed with saturated sodium bicarbonate (3×) and brine (2×)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34bac6f304d54dc8b7cc743ae42e4b2b
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

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