3,4-Dimethylphenol → HCID 18511661, compound

HRID 1370534Notes

Reaction equation

HRID 1370534 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5]Br.[CH3:7][C:8]1[CH:9]=[C:10]([OH:15])[CH:11]=[CH:12][C:13]=1[CH3:14]>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:15][C:10]1[CH:11]=[CH:12][C:13]([CH3:14])=[C:8]([CH3:7])[CH:9]=1

Participants

3

Reactant 2

HCID 72493,4-DimethylphenolHCID 80561,4-Dibromobutane

Product 1

HCID 18511661HCID 18511661, compoundYield 86%

Procedure

1,4-Dibromobutane, condensed with 3,4-dimethylphenol according to Ismaïel et al. (J. Med. Chem., 1993, 36, 2519-25), gives 1-[4-bromobutoxy]-3,4-dimethylbenzene with a yield of 86%. The condensation of this compound (according to the same authors) with 1,4-dioxa-8-azaspiro[4.5]decane gives, after deprotection, 1-[4-(3,4-dimethylphenoxy)butyl]-4-piperidone in the form of an orangey oil with a yield of 61%. The reductive amination of this ketone (4.33 g or 15.7 mmol) with methylamine hydrochloride (1.06 g; 15.7 mmol) in the presence of sodium triacetoxyborohydride (4.33 g; 20.5 mmol) according to the protocol of Example 3.1 makes it possible to prepare 5.95 g (Yd: 63%) of the compound of formula 10:

Sources & evidence

ORD record
ord-e8524fbd4ea44329914b20c029e95ef0
Source dataset
uspto-grants-2003_06
Patent number
US06583159B1

Reaction notes

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