1-Bromo-3-chloropropane → HCID 59457458, compound

HRID 1710770Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[N:12]=2)[CH:5]=[CH:4][C:3]=1[OH:20].Br[CH2:22][CH2:23][CH2:24][Cl:25].C(=O)([O-])[O-].[K+].[K+]>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][N:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[N:12]=2)[CH:5]=[CH:4][C:3]=1[O:20][CH2:22][CH2:23][CH2:24][Cl:25]

Participants

Reactant 3

HCID 80061-Bromo-3-chloropropane

HCID 11430Potassium Carbonate

HCID 136046541HCID 136046541, compound

Product 1

HCID 59457458HCID 59457458, compoundYield 74%

Conditions

Temperature: 50 °C

Procedure

A suspension of 2-chloro-4-[4-(piperidin-1-ylmethyl)-1,3-oxazol-2-yl]phenol i66 (0.13 g, 0.44 mmol, 1 eq), 1-bromo-3-chloropropane (57 μl, 0.58 mmol, 1.3 eq) and potassium carbonate (0.12 g, 0.89 mmol, 2 eq) is stirred at 50° C. overnight. The carbonate is then filtered off and the resulting solution is concentrated under reduced pressure to give 0.12 g of crude 1-({2-[3-chloro-4-(3-chloropropoxy)phenyl]-1,3-oxazol-4-yl}methyl)piperidine i71 as an oil, which is directly used in the next step.

Workup

filtrationThe carbonate is then filtered off
concentrationthe resulting solution is concentrated under reduced pressure

Sources & evidence

ORD record: ord-9bd68b05cf2f47eabda0da4071126c12
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790720B2

Reaction notes

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