Potassium Carbonate → 6-bromo-N-(2-tert-butoxybenzyl)-N-(pyridin-2-ylmethyl)hexan-1-amine

HRID 403116Notes

Reaction equation

HRID 403116 reaction equation
[C:1]([O:5][C:6]1[CH:20]=[CH:19][CH:18]=[CH:17][C:7]=1[CH2:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)([CH3:4])([CH3:3])[CH3:2].[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br.C([O-])([O-])=O.[K+].[K+]>>[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:9]([CH2:8][C:7]1[CH:17]=[CH:18][CH:19]=[CH:20][C:6]=1[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 70896659N-(2-tert-butoxybenzyl)-1-(pyridin-2-yl)methanamine

Product 1

HCID 866726866-bromo-N-(2-tert-butoxybenzyl)-N-(pyridin-2-ylmethyl)hexan-1-amine

Procedure

Compound 10 was synthesized with 9 (2 g, 8.84 mmol), using 1,6-dibromohexane (30 g, 130 mmol) and K2CO3 (1.22 g, 8.84 mmol) following a procedure analogous to that described for 2. Purification was carried out on a silica gel TLC plate that was developed in with a 1% methanolic NH3 (7 M NH3 in methanol/99% CH2Cl2. The product was isolated as pale yellow oil (73%).δ 1H NMR (CDCl3) δ 8.491 (dd, 1H, Ar), 7.630 (t, 1H, Ar), 7.565 (t, 2H, Ar), 7.120 (t, 2H, Ar), 7.020 (t, 2H, Ar), 3.740 (s, 2H, —CH2—), 3.660 (s, 2H, —CH2—), 3.334 (t, 2H, —CH2—), 2.452 (s, 2H, —CH2—), 1.787 (p, 2H, —CH2—), 1.516 (m, 2H, —CH2—), 1.354 (s, 9H, —C(CH3)3), 1.269 (m, 4H). Mass Spec.=435.18 (M+H)+.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-80de1bc1e09149b4bd0eb9fc38690752
Source dataset
uspto-grants-2014_06
Patent number
US08747810B2

Reaction notes

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