Hydrochloric Acid → HCID 22628326, compound

HRID 278440Notes

Reaction equation

HRID 278440 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:7]([CH2:22]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:6]2.[CH3:34][C:35]1[CH:48]=[CH:47][C:38]([CH2:39][C:40]2([OH:46])[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)=[CH:37][CH:36]=1.Cl>C1(C)C=C(C)C=C(C)C=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:13])=[O:14])[CH:7]([CH2:22][N:43]1[CH2:42][CH2:41][C:40]([CH2:39][C:38]3[CH:37]=[CH:36][C:35]([CH3:34])=[CH:48][CH:47]=3)([OH:46])[CH2:45][CH2:44]1)[CH2:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 105362424-(4-Methylbenzyl)-piperidin-4-olHCID 86757886(RS)-Toluene-4-sulfonic acid 5-methoxy-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indol-2-ylmethyl ester

Product 1

HCID 22628326HCID 22628326, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 7947MesityleneSolvent

Procedure

(RS)-Toluene-4-sulfonic acid 5-methoxy-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indol-2-ylmethyl ester (200 mg, 0.41 mmol) and 4-(4-methylbenzyl)-piperidin-4-ol (337 mg, 1.64 mmol) were heated in mesitylene (10 ml) for 20 hr at 140° C. After cooling 4N HCl was added to pHl and the mixture extracted with EtOAc (3×25 ml), the extracts dried (Na2SO4), filtered and evaporated. Purification of the crude material over SiO2 (Merck 230-400 mesh) eluting with EtOAc-cyclohexane-Et3N (9:10:1) afforded the title compound as a yellow oil (155.9 mg, 0.3 mmol, 73%), MS: m/e=521.4 (M+H+).

Workup

  1. additionwas added to pHl and the mixture
  2. extractionextracted with EtOAc (3×25 ml)
  3. dry with materialthe extracts dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification of the crude material over SiO2 (Merck 230-400 mesh)
  7. washeluting with EtOAc-cyclohexane-Et3N (9:10:1)

Sources & evidence

ORD record
ord-d2c53a38edb94e4487d04c8620fea0cf
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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