Potassium Carbonate → Tert-butyl 2-((6-bromohexyl)(2-tert-butoxybenzyl)amino)ethylcarbamate

HRID 403121Notes

Reaction equation

HRID 403121 reaction equation
[C:1]([O:5][C:6]1[CH:23]=[CH:22][CH:21]=[CH:20][C:7]=1[CH2:8][NH:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:4])([CH3:3])[CH3:2].[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]Br.C([O-])([O-])=O.[K+].[K+]>CC#N>[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:9]([CH2:8][C:7]1[CH:20]=[CH:21][CH:22]=[CH:23][C:6]=1[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 70896393Tert-butyl 2-(2-tert-butoxybenzylamino)ethylcarbamate

Product 1

HCID 86672687Tert-butyl 2-((6-bromohexyl)(2-tert-butoxybenzyl)amino)ethylcarbamateYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 14 (3.56 g, 14.6 mmol), 1,6-dibromohexane (35.3 g, 146 mmol) and K2CO3 (2 g, 14.6 mmol) were added to 50 mL CH3CN, and the solution was stirred for 48 h. The solvent was evaporated to dryness and the residue was dissolved in a minimum amount of CH2Cl2 followed by purification via silica gel chromatographed, eluting with a 2% methanolic NH3 (7 M NH3 in methanol/98% CH2Cl2 yield the desired product as a pale yellow oil (64%). 1H NMR (CDCl3) δ 7.354 (dd, 1H, Ar), 7.121 (ddd, 1H, Ar), 7.013 (d, 1H, Ar), 6.986 (t, 1H, Ar), 3.569 (s, 2H, —CH2), 3.351 (t, 2H, —CH2—), 3.145 (d, 2H, —CH2—), 2.507 (t, 2H, —CH2—), 2.399 (t, 2H, —CH2—), 1.805 (p, 2H, —CH2—),1.447 (p, 2H, —CH2—), 1.409 (s, 9H, —C(CH3)3), 1.372 (s, 9H, —C(CH3)3), 1.362 (p, 2H, —CH2—), 1.254 (p, 2H, —CH2—). Mass Spec.=485.48 (M+H)+.

Workup

  1. customThe solvent was evaporated to dryness
  2. dissolutionthe residue was dissolved in a minimum amount of CH2Cl2
  3. customfollowed by purification via silica gel
  4. customchromatographed
  5. washeluting with a 2% methanolic NH3 (7 M NH3 in methanol/98% CH2Cl2

Sources & evidence

ORD record
ord-2527b7e2baf54d2596d1a6d9574a2b44
Source dataset
uspto-grants-2014_06
Patent number
US08747810B2

Reaction notes

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