Potassium Carbonate → Tert-butyl 2-((2-tert-butoxybenzyl)(6-(4-phenylpiperidin-1-yl)hexyl)amino)ethylcarbamate

HRID 403122Notes

Reaction equation

HRID 403122 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].[C:31]1([CH:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[C:27]([O:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH2:19][N:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:40]1[CH2:41][CH2:42][CH:37]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:38][CH2:39]1)[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 698734-PhenylpiperidineHCID 86672687Tert-butyl 2-((6-bromohexyl)(2-tert-butoxybenzyl)amino)ethylcarbamate

Product 1

HCID 70896342Tert-butyl 2-((2-tert-butoxybenzyl)(6-(4-phenylpiperidin-1-yl)hexyl)amino)ethylcarbamateYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound 15 (1.9 g, 4.46 mmol), 4-phenylpiperidine (1.128 g, 6.99 mmol) and K2CO3 (0.64 g, 4.66 mmol) were added to 50 mL CH3CN, and the solution was refluxed under argon atmosphere for 16 h. After cooling to room temperature, the solvent was evaporated to dryness. Purification was carried out on a silica gel TLC plate that was developed in 3% methanolic NH3 (7 M NH3 in methanol)/97% CH2Cl2. The product was obtained as pale yellow oil (73%). 1H NMR (CDCl3) δ 7.382 (d, 1H, Ar), 7.289 (m, 2H, Ar), 7.229 (m, 2H, Ar), 7.186 (m, 1H, Ar), 7.136 (m, 1H, Ar), 7.013 (m, 2H, Ar), 3.587 (s, 2H, —CH2—), 3.160 (m, 2H, —CH2—), 3.071 (d, 2H, —CH2—), 2.519 (overlapping m, 2H, —CH2—), 2.496 (overlapping m, 1H, —CH—), 2.419 (t, 2H, —CH2—), 2.355 (m, 2H, —CH2—), 2.045 (m, 2H, —CH2—), 1.837 (m, 4H, —CH2—CH2—), 1.525 (m, 2H, —CH2—), 1.472 (m, 2H, —CH2—), 1.437 (s, 9H, —C(CH3)3), 1.426 (s, 9H, —C(CH3)3), 1.280 (m, 4H, —CH2—CH2—). Mass Spec=566.43 (M+H)+.

Workup

  1. temperaturethe solution was refluxed under argon atmosphere for 16 h
  2. customthe solvent was evaporated to dryness
  3. customPurification

Sources & evidence

ORD record
ord-8b695ed372034ddabb23d54f8e3fae1b
Source dataset
uspto-grants-2014_06
Patent number
US08747810B2

Reaction notes

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