1-Bromo-3-chloropropane → N-(2-((2-tert-butoxybenzyl)(3-chloropropyl)amino)ethyl)pivalamide

HRID 403130Notes

Reaction equation

HRID 403130 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])OC(C)(C)C)([CH3:4])([CH3:3])[CH3:2].Br[CH2:25][CH2:26][CH2:27][Cl:28].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:1]([O:5][C:6]1[CH:23]=[CH:22][CH:21]=[CH:20][C:7]=1[CH2:8][N:9]([CH2:25][CH2:26][CH2:27][Cl:28])[CH2:10][CH2:11][NH:12][C:13](=[O:19])[C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 70896393Tert-butyl 2-(2-tert-butoxybenzylamino)ethylcarbamate

Product 1

HCID 67128436N-(2-((2-tert-butoxybenzyl)(3-chloropropyl)amino)ethyl)pivalamideYield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 14 (1 g, 4.1 mmol), 1-bromo-3-chloropropane (9.7 g, 60 mmol) and K2CO3 (0.56 g, 4.09 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 purified on a silica gel TLC plate that was developed in 2% methanolic NH3 (7 M NH3 in methanol/98% CH2Cl2 yield the desired product as a pale yellow oil (55%). 1H NMR (CDCl3) δ 7.341 (d, 1H, Ar), 7.139 (dd, 1H, Ar), 7.029 (m, 1H, Ar), 6.995 (m, 1H, Ar), 3.592 (s, 2H, —CH2—), 3.539 (t, 2H, —CH2—), 3.167 (m, 2H, —CH2—), 2.583 (ddd, 2H, —CH2—), 2.519 (ddd, 2H, —CH2—), 1.900 (p, 2H, —CH2—), 1.425 (s, 9H, —C(CH3)3), 1.385 (s, 9H, —C(CH3)3). Mass Spec.=399.96 (M+H)+.

Workup

  1. customThe solvent was evaporated to dryness
  2. customthe residue was purified on a silica gel TLC plate that

Sources & evidence

ORD record
ord-e0053acbb5fc43889d63d0b42d38387f
Source dataset
uspto-grants-2014_06
Patent number
US08747810B2

Reaction notes

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