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

HRID 2053291
Notes
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Reaction equation

HRID 2053291 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. (in the specification, delta, or “Δ,” refers to heat). 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. temperatureto heat)
  2. extractionextracted with, for example, ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried over anhyh
  5. filtrationSubsequent filtration and concentration of the solvent
  6. customprovided the 1 as the yellow-orange oil (1 part by mole)

Sources & evidence

ORD record
ord-e302acb1816f4d00abc7b197530fa390
Source dataset
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07326787B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes