Hydrochloric Acid → 1-(4-Bromophenyl)piperidin-4-one

HRID 715559Notes

Reaction equation

HRID 715559 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 121693418-(4-Bromophenyl)-1,4-dioxa-8-azaspiro[4.5]decane

Product 1

HCID 246921481-(4-Bromophenyl)piperidin-4-one

Conditions

Temperature
50 °C

Procedure

A mixture of 8-(4-bromophenyl)-1,4-dioxa-8-azaspiro[4.5]decane (1.02 g) and half concentrated hydrochloric acid is heated for 12 hours at 50° C., poured on ice and aqueous NaOH solution (4 M) is added until pH ˜7-8. Then the mixture is extracted with ethylacetate and the organic phase is washed with brine and dried (MgSO4). The solvents are evaporated in vacuo to give the title compound. LC (method 2): tR=0.96 min; Mass spectrum (ESI+): m/z=254 [M+H]+.

Workup

  1. additionis added until pH ˜7-8
  2. extractionThen the mixture is extracted with ethylacetate
  3. washthe organic phase is washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solvents are evaporated in vacuo

Sources & evidence

ORD record
ord-e6f97f668b9f407bb0e96ca54852e611
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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