Hydrochloric Acid → HCID 67427609, compound

HRID 1518198Notes

Reaction equation

[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][CH:7]2[CH2:11][CH2:10][CH2:9][N:8]2[CH2:12][CH2:13][CH3:14])=[CH:4][CH:3]=1.[CH:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)([CH3:19])[CH3:18].Cl>N1C=CC=CC=1.ClCCl.C(OCC)(=O)C>[CH:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:1][C:2]2[CH:16]=[CH:15][C:5]([CH2:6][CH:7]3[CH2:11][CH2:10][CH2:9][N:8]3[CH2:12][CH2:13][CH3:14])=[CH:4][CH:3]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1)([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 5 °C

Procedure

2-(4-Aminobenzyl)-1-propylpyrrolidine (300 mg, 1.37 mmol) was dissolved in pyridine-dichloromethane (1:2, 9 mL) and cooled to 5° C. 4-Isopropylbenzenesulfonyl chloride (300 mg, 0.24 mmol) was added and the solution stirred at 5° C. for 18 h. The solution was evaporated, partitioned between ethyl acetate and water, and the organic phase separated and dried over MgSO4. The filtered solution was concentrated and separated by column chromatography (dichloromethane-2% methanol) to give an oil. The oil was dissolved in ethyl acetate and HCl (4M, dioxane) was added to give the product as a white solid (180 mg, 30%).

Workup

customThe solution was evaporated
custompartitioned between ethyl acetate and water
customthe organic phase separated
dry with materialdried over MgSO4
concentrationThe filtered solution was concentrated
customseparated by column chromatography (dichloromethane-2% methanol)
customto give an oil

Sources & evidence

ORD record: ord-e87be3072d604c26afd3ad9717338379
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232426B2

Reaction notes

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