1-Bromo-3-chloropropane → N-(2-tert-butoxybenzyl)-3-chloro-N-(pyridin-2-ylmethyl)propan-1-amine

HRID 403125Notes

Reaction equation

HRID 403125 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[CH2:22][CH2:23][CH2:24][Cl:25].C([O-])([O-])=O.[K+].[K+]>>[C:1]([O:5][C:6]1[CH:20]=[CH:19][CH:18]=[CH:17][C:7]=1[CH2:8][N:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[CH2:22][CH2:23][CH2:24][Cl:25])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 70896659N-(2-tert-butoxybenzyl)-1-(pyridin-2-yl)methanamine

Product 1

HCID 67128530N-(2-tert-butoxybenzyl)-3-chloro-N-(pyridin-2-ylmethyl)propan-1-amine

Procedure

Compound 19 was synthesized with 9 (0.9 g, 3.32 mmol), using 1-bromo-3-chloropropane (10.5 g, 66 mmol) and K2CO3 (0.46 g, 3.32 mmol) following a procedure analogous to that described above for 10. Purification was carried out on a silica-gel column with the following eluents: First with 100% CH2Cl2 and then 2% methanolic NH3 (7 M NH3 in methanol/98% CH2Cl2. The product was isolated as pale yellow oil (65%). 1H NMR (CDCl3) δ 8.491 (m, 1H, Ar), 7.624 (m, 1H, Ar), 7.512 (t, 1H, Ar), 7.111 (m, 2H, Ar), 7.010 (m, 2H, Ar), 3.750 (s, 2H, —CH2—), 3.690 (s, 2H, —CH2—), 3.513 (ddd, 2H, —CH2—), 2.616 (t, 2H, —CH2—), 1.946 (m, 2H, —CH2—), 1.354 (s, 9H, —C(CH3)3). Mass Spec.=346.89 (M+H)+.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-1dd882d0a72d44769a0f2b4def352e38
Source dataset
uspto-grants-2014_06
Patent number
US08747810B2

Reaction notes

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