Ethyl Bromide → HCID 20357511, compound

HRID 2083756Notes

Reaction equation

HRID 2083756 reaction equation
[Mg].Cl[CH:3]1[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1.C(Br)C.[Br:13][C:14]1[CH:27]=[CH:26][C:25]2[S:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:28])[C:16]=2[CH:15]=1.[Cl-].[NH4+]>O1CCCC1>[Br:13][C:14]1[CH:27]=[CH:26][C:25]2[S:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:3]3[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]3)([OH:28])[C:16]=2[CH:15]=1

Participants

7

Reactant 5

HCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 793424-chloro-N-methylpiperidineHCID 3181012-Bromo-10-thiaxanthenoneHCID 5462224Magnesium

Product 1

HCID 20357511HCID 20357511, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 1.2 l g. (0.05 mol) of magnesium turnings covered by tetrahydrofuran in an Argon atmosphere is added about 0.5 g. of 4-chloro-N-methylpiperidine (from 8.5 g., 0.025 mol of the hydrochloride salt) and a small amount of ethyl bromide. The mixture is heated until the reaction is initiated, the remainder of the chloro compound in about 20 ml. of tetrahydrofuran is added and the mixture is refluxed for four hours. 2-Bromothioxanthone (7.3 g., 0.025 mol) is added and the mixture is refluxed for five hours, and then stirred at room temperature 3 days. The reaction mixture is poured into aqueous ammonium chloride and filtered to give 2-bromo-9(1-methyl-4-piperidyl)thioxanthene-9-ol, m.p. 225.5°-226° C.

Workup

  1. additionis added about 0.5 g
  2. temperatureThe mixture is heated until the reaction
  3. temperaturethe mixture is refluxed for four hours
  4. temperaturethe mixture is refluxed for five hours
  5. filtrationfiltered

Sources & evidence

ORD record
ord-665fd8c5b1cd425494e5416da5445bd1
Source dataset
uspto-grants-1978_04
Patent number
US04086350

Reaction notes

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