Dimethylformamide → HCID 12251272, compound

HRID 596283Notes

Reaction equation

[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]21[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]2.[N-:16]=[N+:17]=[N-:18].[Na+].[CH3:20]N(C)C=O>>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:20][CH2:1][C:2]21[CH2:14][CH2:13][CH:12]([N:16]=[N+:17]=[N-:18])[CH2:11][CH2:10]2

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 33557Sodium Azide

HCID 12251437HCID 12251437, compound

Product 1

HCID 12251272HCID 12251272, compound

Procedure

A 3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-ol lower alkyl sulfonate prepared in step (11) and sodium azide in a solvent such as dimethylformamide, on heating (at from about 65° to about 100° C. for from about 4 to about 20 hours); yields a corresponding 3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-ylazide, which on reaction with lithium aluminum hydride in a solvent such as tetrahydrofuran at moderate (room) temperature for from about 3 to about 10 hours, yields a corresponding 3',4'-dihydrospiro(cyclohexane-1,2'(1'H)-naphthalen)-4-ylamine [I(c)] in its free base form. On treating an ether extract of a thus produced compound with an ethereal solution of a suitable (pharmacologically acceptable) acid, its acid addition salt form is obtained.

Sources & evidence

ORD record: ord-4bbede102cb94b66bcf03ce104a3c95e
Source dataset: uspto-grants-1977_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04010201

Reaction notes

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