Hydrochloric Acid → (S)-N-(1-(2-(4-trifluoromethylphenyl)ethyl)pyrrolidin-3-yl)-1-adamantanecarboxamide hydrochloride

HRID 992281Notes

Reaction equation

HRID 992281 reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7]([C:9]23[CH2:18][CH:13]4[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]4)[CH2:10]2)[CH2:16]3)=[O:8])[CH2:2]1.C1(C)C=CC(S(O[CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)(=O)=O)=CC=1.[ClH:42].Cl.C(O)(C)C>>[ClH:42].[F:38][C:37]([F:39])([F:40])[C:34]1[CH:33]=[CH:32][C:31]([CH2:30][CH2:29][N:1]2[CH2:5][CH2:4][C@H:3]([NH:6][C:7]([C:9]34[CH2:18][CH:13]5[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]5)[CH2:10]3)[CH2:16]4)=[O:8])[CH2:2]2)=[CH:36][CH:35]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 18411913HCID 18411913, compoundHCID 21912024Isopropanol hydrochlorideHCID 49760538(S)-N-(pyrrolidin-3-yl)-1-adamantanecarboxamide

Product 1

HCID 86758575(S)-N-(1-(2-(4-trifluoromethylphenyl)ethyl)pyrrolidin-3-yl)-1-adamantanecarboxamide hydrochloride

Procedure

(S)-N-(Pyrrolidin-3-yl)-1-adamantanecarboxamide (0.5 g) and 2-(4-trifluoromethylphenyl)ethyl p-toluenesulfonate (0.69 g) were reacted under the same conditions as in Example 1. After the same post-treatment as in Example 1, the obtained compound was converted to hydrochloride with 30% hydrochloric acid-isopropanol to give (S)-N-(1-(2-(4-trifluoromethylphenyl)ethyl)pyrrolidin-3-yl)-1-adamantanecarboxamide hydrochloride 1/2 hydrate (0.51 g), melting point 214-215° C.

Sources & evidence

ORD record
ord-4cc91c93e68949cfaee2259b9bf54c04
Source dataset
uspto-grants-2002_10
Patent number
US06468998B1

Reaction notes

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