HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1500335
Notes
Print preview

Reaction equation

HRID 1500335 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)carbamate

Reagents, catalysts & solvents 3

HCID 176Acetic 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.

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

Sources & evidence

ORD record
ord-f48332a52b454c169cd377fc55151a00
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09206156B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes