2,2-Diethoxyethylamine → HCID 12707053, compound

HRID 973038Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=1)[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:25][CH2:26][CH:27]([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30]>O>[CH2:18]([O:17][C:15]1[CH:14]=[C:11]([CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:16]=1)[CH:12]=[N:25][CH2:26][CH:27]([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4.6 g of 3,5-dibenzyloxybenzaldehyde are added to 3.0 g of 1-amino-2,2-diethoxyethane, and the mixture is heated at 100° C for 10 minutes. Then, the mixture is stirred at 60° C for 2.5 hours under reduced pressure until water is removed from the mixture. 6.3 g of 1-[N-(3,5-dibenzyloxybenzylidene)amino]-2,2-diethoxyethane is thereby obtained as an oil. 5.9 g of this product are dissolved in 100 ml of ethanol. 600 mg of sodium borohydride are added to the ethanol solution, and the mixture is refluxed for 2 hours. After the reaction, water is added to the mixture and the aqueous mixture is extracted with ethyl acetate. The extract is dried and then evaporated to remove solvent, whereby 5.9 g of 1-[N-(3,5-dibenzyloxybenzyl)amino]-2,2-diethoxyethane are obtained.

Workup

customis removed from the mixture

Sources & evidence

ORD record: ord-7ae8c77a0f604c888d95f02247b0c37a
Source dataset: uspto-grants-1977_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04054659

Reaction notes

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