1,5-Dibromopentane → HCID 21539612, compound

HRID 1076255Notes

Reaction equation

HRID 1076255 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][Br:7].[CH3:8][C:9]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)([CH3:12])[CH2:10][OH:11].C(=O)([O-])[O-].[K+].[K+]>C(O)CCC>[CH3:12][C:9]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[CH:22][C:23]([NH:26][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][Br:7])=[CH:24][CH:25]=2)=[CH:16][CH:15]=1)([CH3:8])[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 21539605HCID 21539605, compound

Product 1

HCID 21539612HCID 21539612, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

23 g. of 1,5-dibromopentane, 25.7 g. of 2-methyl-2-[4-(4-aminophenyl)-phenoxy]-propanol (obtainable by reaction of 4-hydroxy-4'-nitro-diphenyl with 2-bromo-2-methylpropanol to 2-methyl-2-[4-(4-nitrophenyl)-phenoxy]-propanol and reduction), and 27 g. of potassium carbonate are refluxed in 400 ml. of n-butanol for 12 hours. 2-Methyl-2-[4-(p-5-bromopentylaminophenyl)-phenoxy]-propanol is formed as the intermediate, which is not isolated. Then, the solvent is distilled off, the residue mixed with water and extracted with ethyl acetate. After drying and evaporation, 2-methyl-2-[4-(4-piperidinophenyl)-phenoxy]-propanol is obtained, m.p. 158°-160°.

Sources & evidence

ORD record
ord-155b7924af304124a951610b7cf7da18
Source dataset
uspto-grants-1976_05
Patent number
US03956334

Reaction notes

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