2,2-Diethoxyethylamine → HCID 12707055, compound

HRID 973037Notes

Reaction equation

HRID 973037 reaction equation
C(OC1C=C(C=C(OCC2C=CC=CC=2)C=1)C=O)C1C=CC=CC=1.NCC(OCC)OCC.[CH2:34]([O:41][C:42]1[CH:43]=[C:44]([CH:55]=[C:56]([O:58][CH2:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[CH:57]=1)[CH:45]=[N:46][CH2:47][CH:48]([O:52][CH2:53][CH3:54])[O:49][CH2:50][CH3:51])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[BH4-].[Na+]>C(O)C>[CH2:34]([O:41][C:42]1[CH:43]=[C:44]([CH:55]=[C:56]([O:58][CH2:59][C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)[CH:57]=1)[CH2:45][NH:46][CH2:47][CH:48]([O:49][CH2:50][CH3:51])[O:52][CH2:53][CH3:54])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 695242,2-DiethoxyethylamineHCID 5613513,5-DibenzyloxybenzaldehydeHCID 4311764Sodium borohydrideHCID 12707053HCID 12707053, compound

Product 1

HCID 12707055HCID 12707055, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[N-(3,5-dibenzyloxybenzyl)-N-p-tosyl-amino]-2,2-diethoxyethane (VI) is readily obtainable. For example, said compound (VI) is prepared by condensing 3,5-dibenzyloxybenzaldehyde with 1-amino-2,2-diethoxyethane at 60° to 100° C, reducing the resultant 1-[N-(3,5-dibenzyloxybenzylidene)amino]-2,2-diethoxyethane with sodium borohydride in ethanol under refluxing to give 1-[N-(3,5-dibenzyloxybenzyl)amino]-2,2-diethoxyethane, and then reacting said product with p-tosyl chloride in pyridine under ice-cooling.

Workup

  1. temperatureunder refluxing

Sources & evidence

ORD record
ord-2645dfb9c7de40aab5ae85c7981d3f68
Source dataset
uspto-grants-1977_10
Patent number
US04054659

Reaction notes

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