Potassium Cyanide → HCID 21553920, compound

HRID 267786Notes

Reaction equation

[NH2:1][CH:2]1COC2C=CC=C(OCC3C=CC=CC=3)C=2OC1C#N.[O:23]=[C:24]1[CH2:30][O:29][C:28]2[CH:31]=[CH:32][CH:33]=[C:34]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:27]=2[O:26][CH2:25]1.[C-]#N.[K+]>>[OH:23][C:24]1([C:2]#[N:1])[CH2:30][O:29][C:28]2[CH:31]=[CH:32][CH:33]=[C:34]([O:35][CH2:36][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:27]=2[O:26][CH2:25]1

Participants

Reactant 3

HCID 9032Potassium Cyanide

HCID 21553945HCID 21553945, compound

HCID 21553969HCID 21553969, compound

Product 1

HCID 21553920HCID 21553920, compound

Procedure

The 3-amino-4-cyano-6-benzyloxy-3,4-dihydro-2H-1,5-benzodioxepin and/or its 9-benzyloxy isomer is converted to 3-oxo-6-benzyloxy-3,4-dihydro-2H-1,5-benzodioxepin by the procedure described in Example 1, Step C, and the 3-keto compound then reacted with potassium cyanide by either the process of Step D of Example 1 or the alternative procedure there described to provide 3-hydroxy-3-cyano-6-benzyloxy-3,4-dihydro-2H-1,5-benzodioxepin. This product then is reduced with lithium aluminum hydride by the method outlined in the alternate of Step E, Example 1, to give 3-hydroxy-3-aminomethyl-6-benzyloxy-3,4-dihydro-2H-1,5-benzodioxepin which when reacted with acetone and then reduced by the process of Step F, Example 1, there is obtained 3,6-dihydroxy-3-isopropylaminomethyl-3,4-dihydro-2H-1,5-benzodioxepin hydrochloride.

Sources & evidence

ORD record: ord-3b6cc185a6fe448b9211184e5cad41fc
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03944560

Reaction notes

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