Sulfuric Acid → HCID 178461315, compound

HRID 1881098Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O.[Cl:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][C:21]([NH:23][C@H:24]2[CH2:29][CH2:28][C@H:27]([CH3:30])[CH2:26][CH2:25]2)=O)[CH:16]=[CH:17][CH:18]=1>C1COCC1>[Cl:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][CH2:21][NH:23][C@H:24]2[CH2:25][CH2:26][C@H:27]([CH3:30])[CH2:28][CH2:29]2)[CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1M Lithium aluminium hydride (5 mL, 5 mmol) and dry THF (5 mL) was cooled to 0° C. where upon 98% sulphuric acid (133 μL, 2.5 mmol) was added over a period of 10 min. The resulting solution was stirred for 10 min at 0° C. and then allowed to warm to room temperature over 30 min. 3-(3-Chloro-phenyl)-N-(trans-4-methyl-cyclohexyl)-propionamide (900 mg, 3.2 mmol) in THF (6 mL) was added and the solution stirred for 16 h at room temperature. The reaction was quenched by the sequential addition of water (190 μL), 4N NaOH (190 μL) and water (190 μL). Dilution with THF (25 mL) followed by the addition of MgSO4 (5 g), filtration and concentration in vacuo yielded 700 mg of [3-(3-Chloro-phenyl)-propyl]-(trans-4-methyl-cyclohexyl)-amine.

Workup

additionwas added over a period of 10 min
temperatureto warm to room temperature over 30 min
stirringthe solution stirred for 16 h at room temperature
customThe reaction was quenched by the sequential addition of water (190 μL), 4N NaOH (190 μL) and water (190 μL)
additionDilution with THF (25 mL) followed by the addition of MgSO4 (5 g), filtration and concentration in vacuo

Sources & evidence

ORD record: ord-9b6f3a9cc9b04e85988c74569631dcde
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318778B2

Reaction notes

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