Hydrochloric Acid → SiraMesine, Lu-28-179

HRID 1760546Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH2:17][CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][C:24]4([C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH2:28][O:27]4)[CH2:23][CH2:22]3)=[CH:9]2)=[CH:4][CH:3]=1.[ClH:35]>>[ClH:35].[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH2:17][CH2:18][CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][C:24]4([C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH2:28][O:27]4)[CH2:25][CH2:26]3)=[CH:9]2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 9829526Siramesine

Product 1

HCID 9891778SiraMesine, Lu-28-179

Conditions

Temperature: 45 °C

Procedure

1′-[4-[1-(4-fluorophenyl)-1H-indole-3-yl]-1-butyl]-spiro[isobenzofuran-1(3H),4′-piperidine] (10.3 g) and 2-propanole (100 ml) were heated to reflux. The solution was allowed to cool to 45° C. Aqueous hydrochloric acid (2.2 ml, 36%) was added dropwise and a precipitate of the title compound was formed. The suspension was heated to reflux and allowed to cool to ambient temperature. The suspension was cooled in ice, filtered off and dried. Yield: 10.1 g (90%). The salt is a mono salt and according to our investigations an anhydrate. KF: 0.51%; HPLC 100.8%; DSC (onset/peakmax) 222.5° C./223.8° C. CHN (calculated/measured): C: 73.38/73.13; H: 6.57/6.56; N: 5.70/5.80.

Sources & evidence

ORD record: ord-9a150b695d7a4ff3a4c5d5d4c2763d0f
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06844352B2

Reaction notes

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