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tert-butyl N-methyl-N-(3-oxopropyl)carbamate → Tert-butyl 3-(4-(dimethylamino)-4-phenylpiperidin-1-yl)propyl(methyl)carbamate

HRID 453896
Notes
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Reaction equation

HRID 453896 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][CH:12]=O)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].Cl.Cl.[CH3:16][N:17]([CH3:30])[C:18]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(B)#N.[Na]>CO.C(O)(=O)C.CO.C(Cl)(Cl)Cl>[CH3:16][N:17]([CH3:30])[C:18]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][CH2:20][N:21]([CH2:12][CH2:11][CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6])[CH2:22][CH2:23]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10442454tert-butyl N-methyl-N-(3-oxopropyl)carbamateHCID 67366566N,N-dimethyl-4-phenylpiperidin-4-amine dihydrochlorideHCID 101953985CID 1019539852×

Product 1

HCID 68494485Tert-butyl 3-(4-(dimethylamino)-4-phenylpiperidin-1-yl)propyl(methyl)carbamateYield 60.4%

Reagents, catalysts & solvents 3

HCID 176
Acetic Acid
Solvent
2×
HCID 887MethanolSolvent
HCID 21584188Chloroform methanolSolvent

Conditions

Temperature
0 °C

Procedure

11.1 g (1.3 eq.) tert-butyl methyl(3-oxopropyl)carbamate were added to a solution of 11 g (1 eq.) N,N-dimethyl-4-phenylpiperidin-4-amine dihydrochloride in 110 ml methanol at 0° C. and the reaction mixture was stirred for 15 min at 0° C. 6.2 g (3 eq.) sodium cyanoboron hydride were then added in portions and the mixture was stirred for 30 min at room temperature. The reaction mixture obtained was adjusted to a pH of 5-6 with acetic acid and stirred for 12 h at room temperature. The reaction course was monitored by thin-layer chromatography (20% MeOH/CHCl3). As the conversion was still not complete, 2.4 g sodium cyanoboron hydride were added and the reaction mixture obtained was adjusted to pH 5-6 with acetic acid and stirred for 60 min at room temperature. Once the conversion was complete, the methanol was distilled off, the mixture was made alkaline with saturated NaHCO3 solution, the mixture obtained was extracted with chloroform (3×100 ml) and the combined organic phases were dried over Na2SO4. Following removal of the solvent under reduced pressure, the residue was purified by column chromatography (silica gel; 5% MeOH/CHCl3). 9 g (60%) of product were obtained.

Workup

  1. stirringthe mixture was stirred for 30 min at room temperature
  2. customThe reaction mixture obtained
  3. stirringstirred for 12 h at room temperature
  4. customthe reaction mixture obtained
  5. stirringstirred for 60 min at room temperature
  6. distillationthe methanol was distilled off
  7. customthe mixture obtained
  8. extractionwas extracted with chloroform (3×100 ml)
  9. dry with materialthe combined organic phases were dried over Na2SO4
  10. customremoval of the solvent under reduced pressure
  11. customthe residue was purified by column chromatography (silica gel; 5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-1dc9030852d44bd5a14d9547d94dfdd9
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492559B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes