4-Chlorobenzylamine → HCID 9191511, compound

HRID 2110827Notes

Reaction equation

HRID 2110827 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1.ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>O1CCCC1>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:23][C:14]([CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]2)=[O:16])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 660364-ChlorobenzylamineHCID 181649HOAtHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 9191511HCID 9191511, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-t-butoxycarbonyl-4-carboxypiperidine (2.3 g, 10 mmol), 4-chlorobenzylamine (1.56 g, 11 mmol), and 1-hydroxy-7-azabenzotriazole (1.5 g, 11 mmol) in tetrahydrofuran (20 mL) at room temperature under argon, was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (2.1 g, 11 mmol), and the resulting mixture was stirred for 16 h. The solvent was evaporated under vacuum, and the residue was dissolved in ethyl acetate (50 mL). The resulting solution was washed sequentially with 0.01 M aqueous hydrochloric acid (50 mL), 1.0 M aqueous sodium hydroxide (25 mL), and brine (25 mL) before drying (anhydrous sodium sulfate) and evaporation under vacuum to obtain 4-(N-(4-chlorobenzyl)aminocarbonyl)-1-t-butoxycarbonylpiperidine (3.6 g, quantitative yield).

Workup

  1. customThe solvent was evaporated under vacuum
  2. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
  3. washThe resulting solution was washed sequentially with 0.01 M aqueous hydrochloric acid (50 mL), 1.0 M aqueous sodium hydroxide (25 mL), and brine (25 mL)
  4. custombefore drying
  5. custom(anhydrous sodium sulfate) and evaporation under vacuum

Sources & evidence

ORD record
ord-293de4784a2a40cab560672a7cebaaef
Source dataset
uspto-grants-2009_04
Patent number
US07517991B2

Reaction notes

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