4-(1-Pyrrolidinyl)piperidine → [3,5-Bis-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 1517083Notes

Reaction equation

HRID 1517083 reaction equation
FC(F)(F)C1C=C(C2C(C(O)=O)=NC=C(C3C=CC=C(C(F)(F)F)C=3)C=2)C=CC=1.C[O:31][C:32]([C:34]1[C:39]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:49])([F:48])[F:47])[CH:41]=2)=[CH:38][C:37]([C:50]2[CH:55]=[CH:54][CH:53]=[C:52]([C:56]([F:59])([F:58])[F:57])[CH:51]=2)=[CH:36][N:35]=1)=O.CC1C(C(O)=O)=NC=C(C2C=CC=C(C(F)(F)F)C=2)C=1.[N:80]1([CH:85]2[CH2:90][CH2:89][NH:88][CH2:87][CH2:86]2)[CH2:84][CH2:83][CH2:82][CH2:81]1>>[F:47][C:46]([F:49])([F:48])[C:42]1[CH:41]=[C:40]([C:39]2[C:34]([C:32]([N:88]3[CH2:89][CH2:90][CH:85]([N:80]4[CH2:84][CH2:83][CH2:82][CH2:81]4)[CH2:86][CH2:87]3)=[O:31])=[N:35][CH:36]=[C:37]([C:50]3[CH:55]=[CH:54][CH:53]=[C:52]([C:56]([F:58])([F:59])[F:57])[CH:51]=3)[CH:38]=2)[CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 4

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 574411243-Methyl-5-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acidHCID 574411353,5-Bis-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl ester2×HCID 574411503,5-Bis-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid

Product 1

HCID 58016720[3,5-Bis-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Procedure

In analogy to the procedure described for example 1, 3,5-bis-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid [prepared from 3,5-bis-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl ester (intermediate 8) by saponification in analogy to the procedure described for intermediate 1B] was reacted with 4-pyrrolidin-1-yl-piperidine to give the title compound as light yellow oil. MS: 548.3 (MH+).

Sources & evidence

ORD record
ord-fc7e83c07d334f659dee4201ca4ea42d
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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