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Potassium Iodide → Ethyl 4-(dibenzylamino)-3-methoxypiperidine-1-carboxylate

HRID 38444
Notes
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Reaction equation

HRID 38444 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH:3]1[O:13][CH3:14].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C.O>[CH2:15]([N:1]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH:3]1[O:13][CH3:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 3019430Ethyl 4-amino-3-methoxypiperidine-1-carboxylate

Product 1

HCID 19994850Ethyl 4-(dibenzylamino)-3-methoxypiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of racemic ethyl 4-amino-3-methoxypiperidine-1-carboxylate (1 part by mole) in DMF were added benzyl bromide (about 2.2 part by mole), potassium carbonate (about 2.4 part by mole) and potassium iodide (about 0.2 part by mole) respectively. The reaction was heated to about 80° C. After about 6 hours, the reaction was slowly diluted with water (about 12 parts by volume) and extracted with, for example, ethyl acetate. The organic layer was washed with brine and then dried over anhyh. Na2SO4. Subsequent filtration and concentration of the solvent provided the 1 as the yellow-orange oil (1 part by mole).

Workup

  1. extractionextracted with, for example, ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried over anhyh
  4. filtrationSubsequent filtration and concentration of the solvent
  5. customprovided the 1 as the yellow-orange oil (1 part by mole)

Sources & evidence

ORD record
ord-17a54a287d1e4126a5549dd620dd2994
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524736B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes