Dimethyl Sulfoxide → HCID 12894308, compound

HRID 436321Notes

Reaction equation

[H-].[Na+].CS(C)=O.[CH3:7][C:8]1[NH:9][C:10]([CH3:21])=[C:11]2[C:15]([CH3:18])([C:16]#[N:17])[CH2:14][C:13]([CH3:20])([CH3:19])[C:12]=12.Cl.Cl[CH2:24][CH2:25][CH2:26][N:27]([CH3:29])[CH3:28]>O>[CH3:28][N:27]([CH3:29])[CH2:26][CH2:25][CH2:24][N:9]1[C:10]([CH3:21])=[C:11]2[C:15]([CH3:18])([C:16]#[N:17])[CH2:14][C:13]([CH3:20])([CH3:19])[C:12]2=[C:8]1[CH3:7]

Participants

Conditions

Temperature: 15 °C

Procedure

To a solution prepared by heating 23.2 g. (0.55 mole) of a 67% mineral oil dispersion of sodium hydride in 200 ml. of anhydrous dimethylsulfoxide was added 50.5 g. (0.25 mole) of the 2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile described above in Example 3. The mixture was stirred under nitrogen for about two hours, cooled to 15° C., and treated with 39.5 g. (0.25 mole) of 3-chloro-N,N-dimethylpropylamine hydrochloride. When the foaming had subsided, the mixture was stirred at room temperature overnight, poured into water, and the gummy solid which separated was taken into diethyl ether and the solution washed first with water, then with saturated brine, dried and taken to dryness to give 69 g. of a solid which was recrystallized once from hexane and once from isopropanol to give 29 g of 2-[3-(di-methylamino)propyl]-2,4,5,6-tetrahydro-1,3,4,6,6-pentamethylcyclopenta[c]pyrrole-4-carbonitrile, m.p. 90.5°-91.0° C.

Workup

customTo a solution prepared
temperatureby heating 23.2 g
additiontreated with 39.5 g
stirringthe mixture was stirred at room temperature overnight
customthe gummy solid which separated
washthe solution washed first with water
dry with materialwith saturated brine, dried
customto give 69 g
customof a solid which was recrystallized once from hexane and once from isopropanol

Sources & evidence

ORD record: ord-178efedd958d4bcd8e765f2552e4bad8
Source dataset: uspto-grants-1977_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04008250

Reaction notes

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