Ammonium Chloride → Tert-butyl 4-{2-[3-(aminocarbonyl)phenyl]ethyl}-1-piperidinecarboxylate

HRID 2074299Notes

Reaction equation

HRID 2074299 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]2[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=2)[C:19](O)=[O:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C[N:27](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[Cl-].[NH4+].C(=O)([O-])O.[Na+]>CN(C=O)C>[NH2:27][C:19]([C:18]1[CH:17]=[C:16]([CH2:15][CH2:14][CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]2)[CH:24]=[CH:23][CH:22]=1)=[O:20]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574218263-{2-[1-(Tert-butoxycarbonyl)-4-piperidinyl]ethyl]benzoic acid

Product 1

HCID 57421827Tert-butyl 4-{2-[3-(aminocarbonyl)phenyl]ethyl}-1-piperidinecarboxylateYield 60.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-{2-[1-(Tert-butoxycarbonyl)-4-piperidinyl]ethyl}benzoic acid (17.8 g) was dissolved in DMF (200 ml), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (15.4 g) and 1-hydroxybenzotriazole (10.8 g) were added thereto, followed by stirring at room temperature for 2 hours. Ammonium chloride (8.57 g) and TEA (22.3 ml) were added to the reaction liquid, followed by stirring overnight at room temperature. An aqueous saturated sodium hydrogencarbonate solution was added to the reaction liquid, and the precipitated crystal was collected by filtration and dried to obtain tert-butyl 4-{2-[3-(aminocarbonyl)phenyl]ethyl}-1-piperidinecarboxylate (10.8 g).

Workup

  1. stirringby stirring overnight at room temperature
  2. filtrationthe precipitated crystal was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-5ee10ee441974b25a35db9a5fbc55643
Source dataset
uspto-grants-2011_04
Patent number
US07919495B2

Reaction notes

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