Diisopropyl Ether → 4-Aminomethyl-1-(pyridin-4-yl)piperidine-4-carboxylic acid ethyl ester dihydrobromide

HRID 412607Notes

Reaction equation

HRID 412607 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:18][NH:19]C(OCC2C=CC=CC=2)=O)[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[BrH:30].C(O)(=O)C.CCCCCC.C(OC(C)C)(C)C>C(Cl)(Cl)Cl.C(OCC)C>[BrH:30].[BrH:30].[CH2:1]([O:3][C:4]([C:6]1([CH2:18][NH2:19])[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 8058HexaneHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 600641284-Benzyloxycarbonylaminomethyl-1-(pyridin-4-yl)piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 696973274-Aminomethyl-1-(pyridin-4-yl)piperidine-4-carboxylic acid ethyl ester dihydrobromide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 4-benzyloxycarbonylaminomethyl-1-(pyridin-4-yl)piperidine-4-carboxylic acid ethyl ester (331 mg) in chloroform (0.5 ml) was added 25% hydrogen bromide-acetic acid (2 ml), and the mixture was stirred at room temperature for 10 min. After completion of the reaction, hexane, diisopropyl ether and diethyl ether were added and the supernatant was removed. Then, dimethylformamide (1 ml) was added and the resultant solid was collected by filtration, and washed with diethyl ether and dried under reduced pressure to give the title compound (423 mg).

Workup

  1. additionwere added
  2. customthe supernatant was removed
  3. additionThen, dimethylformamide (1 ml) was added
  4. filtrationthe resultant solid was collected by filtration
  5. washwashed with diethyl ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-638c12e62b5b49f0942c0610889731d2
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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