Sodium Carbonate → Isopropyl alcohol isopropyl ether

HRID 839782Notes

Reaction equation

Cl.[CH3:2][CH:3]1NC[C:6]2[CH:9]=[CH:10]SC=2[CH2:4]1.C[O:13][C:14]([C:16]1[CH:23]=CC=CC=1CBr)=O.C(=O)([O-])[O-:25].[Na+].[Na+]>CN(C)C=O>[CH:3]([OH:13])([CH3:4])[CH3:2].[CH:16]([O:25][CH:9]([CH3:6])[CH3:10])([CH3:14])[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-methyl-4,5,6,7-tetrahydro-thieno[3,2-c]-pyridine hydrochloride (7.05 g; 37.2 mmoles), o-methoxycarbonylbenzyl bromide (9 g; 39.3 mmoles) and sodium carbonate (6.05 g; 57 mmoles) in dimethylformamide (100 cc) is stirred during 3 hours at 80° C. After cooling, the inorganic salts are filtered off and the filtrate is evaporated to dryness. The residue is dissolved in ether and the ether solution is washed with water and dried over sodium sulfate, after which the ether is evaporated off. The resulting yellow oil is treated with an equivalent amount of hydrogen chloride gas in ether solution. The hydrochloride is filtered off and recrystallized from isopropyl alcohol-diisopropyl ether (M.p. = 166° C. Yield: 53%).

Workup

temperatureAfter cooling
filtrationthe inorganic salts are filtered off
customthe filtrate is evaporated to dryness
dissolutionThe residue is dissolved in ether
washthe ether solution is washed with water
dry with materialdried over sodium sulfate
customafter which the ether is evaporated off
additionThe resulting yellow oil is treated with an equivalent amount of hydrogen chloride gas in ether solution
filtrationThe hydrochloride is filtered off

Sources & evidence

ORD record: ord-b42e70deb89a4738b82b1fbb577574fc
Source dataset: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04097482

Reaction notes

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