Water → HCID 9843070, compound

HRID 1250729Notes

Reaction equation

HRID 1250729 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH3:3].[OH-].[Na+].O.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>O1CCCC1.CCOCC>[CH2:25]([O:24][C:22]([N:15]1[CH2:14][CH2:13][CH:12]([S:11][C:8]2[CH:7]=[CH:6][C:5]([CH2:4][N:2]([CH3:1])[CH3:3])=[CH:10][CH:9]=2)[CH2:17][CH2:16]1)=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformate2×HCID 14798Sodium Hydroxide2×HCID 11747081HCID 11747081, compound

Product 1

HCID 9843070HCID 9843070, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

250 mg (1 mmol) of 4-[4-(dimethylaminomethyl)phenylthio]piperidine in 20 ml tetrahydrofuran are combined with 2 ml 2N sodium hydroxide solution and 5 ml water. At ambient temperature 200 mg (1.2 mmol) of benzyl chloroformate in 5 ml tetrahydrofuran are slowly added dropwise. After 1.5 hours at ambient temperature some benzyl chloroformate and sodium hydroxide solution are again added. After the addition of 100 ml ether the mixture is washed with saturated saline solution, the organic phase is dried with magnesium sulphate and concentrated by evaporation. The product obtained after purification by column chromatography (aluminium oxide, petroleum ether/ethyl acetate=4:1, v:v) is converted into the hydrochloride with ethereal hydrochloric acid. 190 mg (45.1% of theory) of the title compound are obtained as a colourless powder, melting point 144° C.

Workup

  1. washis washed with saturated saline solution
  2. dry with materialthe organic phase is dried with magnesium sulphate
  3. concentrationconcentrated by evaporation
  4. customThe product obtained
  5. customafter purification by column chromatography (aluminium oxide, petroleum ether/ethyl acetate=4:1, v:v)

Sources & evidence

ORD record
ord-884daf411c5b41bd8f21c4f26dbc5646
Source dataset
uspto-grants-2002_01
Patent number
US06339096B1

Reaction notes

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