Sodium Hydroxide → Dibenzyl-[3-(2-benzyloxy-ethoxy)-propyl]-amine

HRID 410978Notes

Reaction equation

HRID 410978 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11]S(C1C=CC(C)=CC=1)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([N:29]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:30][CH2:31][CH2:32]O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:34]([N:29]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:30][CH2:31][CH2:32][O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5613752-(Benzyloxy)ethyl 4-methylbenzenesulfonateHCID 44370073-(Dibenzylamino)-1-propanol

Product 1

HCID 67332452Dibenzyl-[3-(2-benzyloxy-ethoxy)-propyl]-amineYield 29.7%

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

Dibenzyl-[3-(2-benzyloxy-ethoxy)-propyl]-amine (378 mg) was prepared by following General Procedure W starting from toluene-4-sulfonic acid 2-benzyloxy-ethyl ester (1.0 g), 3-dibenzylamino-propan-1-ol (1.08 g), 50% aqueous sodium hydroxide solution (1.3 g in 1.3 mL of water), and tetrabutylammonium hydrogen sulfate (111 mg).

Sources & evidence

ORD record
ord-855ab1d47c4d4a2a97e8c4ac842ee0c1
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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