Potassium Carbonate → 2-Bromomethylnaphthalene

HRID 1005063Notes

Reaction equation

HRID 1005063 reaction equation
C(N1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16](O)[CH:15]=2)C(O)C1)C1C=CC=CC=1.[Br:22][CH2:23]CCOC1CCCCO1.[C:33](=O)([O-])[O-].[K+].[K+].C(N1CCC(C2C=CC=C(OCCCOC3CCCCO3)C=2)C(O)C1)C1C=CC=CC=1>CC(C)=O.CCCCCC>[Br:22][CH2:23][C:13]1[CH:12]=[CH:11][C:14]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:33]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 22127008HCID 22127008, compoundHCID 22128179HCID 22128179, compound

Product 1

HCID 703202-Bromomethylnaphthalene

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8058HexaneSolvent

Procedure

In an analogous manner to that described in Example 14, by alkylating (3RS,4RS)-1-benzyl-4-(3-hydroxy-phenyl)-piperidin-3-ol with rac.-2-(3-bromo-propoxy)-tetrahydro-pyran in the presence of potassium carbonate there was obtained a mixture of the diastereomeric racemates of (3RS,4RS)-1-benzyl-4-{3-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-phenyl}-piperidin-3-ol as a colourless oil; Rf : 0.38 (hexane:acetone=1:1). Subsequent alkylation with 2-bromomethylnaphthalene analogously to Example 12(b) gave a mixture of the diastereomeric racemates of 1-benzyl-3-(naphthalen-2-ylmethoxy)-4-{3-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-phenyl}-piperidine as a colourless oil; MS: 566 (M+H)+. Subsequent reaction with 2,2,2-trichloroethyl (sic) chloroformate analogously to Example 12(c) yielded a mixture of the diastereomeric racemates of 2,2,2-trichloroethyl 3-(naphthalen-2-ylmethoxy)-4-{3-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-phenyl}-piperidine-1-carboxylate which, without further purification and characterization, was reacted with p-toluenesulphonic acid analogously to Example 53(c) to give 2,2,2-trichloroethyl (3RS,4RS)-4-[3-(3-hydroxy-propoxy)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate. Finally, by reaction with pyridine-2-carbonyl azide in an analogous manner to that described in Example 24(m) there was obtained 2,2,2-trichloroethyl (3RS,4RS)-3-(naphthalen-2-ylmethoxy)-4-{3-[3-(pyridin-2-ylcarbamoyloxy)-propoxy]-phenyl}-piperidine-1-carboxylate as a colourless oil; Rf : 0.55 (methylene chloride:ethyl acetate=1:1).

Workup

  1. customthere was obtained

Sources & evidence

ORD record
ord-242d759987d842848ed888e63b7a5ef2
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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