Sulfuric Acid → HCID 10815838, compound

HRID 1587103Notes

Reaction equation

HRID 1587103 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([CH2:13][C:14]#[N:15])[CH:10]=[CH:9][C:5]=1[C:6]([O-:8])=[O:7])[CH3:2].[CH:16]1([CH2:22][CH:23](O)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.S(=O)(=O)(O)[OH:38].Cl[C:43]1[CH:48]=CC=CC=1Cl>>[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([CH2:13][C:14]([NH:15][CH:23]([CH2:22][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:38])[CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH2:48][CH3:43])=[O:7])[CH3:2]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 72391,2-Dichlorobenzene2×HCID 21261766HCID 21261766, compoundHCID 54424526HCID 54424526, compound

Product 1

HCID 10815838HCID 10815838, compound

Procedure

At 23°-25° C., a solution of 2-ethoxy-4-cyanomethyl-benzoate (2.35 g, 10 mmol) and α-cyclohexylmethyl-2-piperidino-benzyl alcohol (2.88 g, 10 mmol) in o-dichlorobenzene (15 ml) is added dropwise to a mixture of concentrated sulphuric acid (15 ml) and o-dichlorobenzene (15 ml). The mixture is stirred for 2 hours at ambient temperature. The o-dichlorobenzene phase is then separated off and the residue is added to ice. After being made alkaline with soda solution, it is extracted with chloroform. The extracts are dried over sodium sulphate and concentrated by evaporation. The residue is purified by column chromatography on silica gel (toluene/acetone=10/1).

Workup

  1. customThe o-dichlorobenzene phase is then separated off
  2. additionthe residue is added to ice
  3. extractionis extracted with chloroform
  4. dry with materialThe extracts are dried over sodium sulphate
  5. concentrationconcentrated by evaporation
  6. customThe residue is purified by column chromatography on silica gel (toluene/acetone=10/1)

Sources & evidence

ORD record
ord-7c364d268b98430b8b1c81065117ecf9
Source dataset
uspto-grants-1993_06
Patent number
US05216167

Reaction notes

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