Triethylamine → (1R*,2R*,5S*,6R*)-6-[(4-Benzylpiperazin-1-yl)carbonyl]-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane

HRID 2088194Notes

Reaction equation

HRID 2088194 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]([F:40])([F:39])[C:10]1[CH:11]=[C:12]([CH2:20][O:21][C@@H:22]2[CH2:28][CH2:27][C@@H:26]3[NH:29][C@@:23]2([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:24][C@H:25]3[C:30]([OH:32])=O)[CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1.[CH2:41]([N:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>>[CH2:41]([N:48]1[CH2:53][CH2:52][N:51]([C:30]([C@@H:25]2[CH2:24][C@:23]3([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[NH:29][C@H:26]2[CH2:27][CH2:28][C@H:22]3[O:21][CH2:20][C:12]2[CH:11]=[C:10]([C:9]([F:39])([F:8])[F:40])[CH:15]=[C:14]([C:16]([F:18])([F:19])[F:17])[CH:13]=2)=[O:32])[CH2:50][CH2:49]1)[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 759941-BenzylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86586738(1R*,2R*,5S*,6R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octan-6-carboxylic acid trifluoroacetate

Product 1

HCID 86586739(1R*,2R*,5S*,6R*)-6-[(4-Benzylpiperazin-1-yl)carbonyl]-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octaneYield 85%

Procedure

A mixture of (1R*,2R*,5S*,6R*)-2-[3,5-bis(trifluoromethyl)phenyl]methoxy)-1-phenyl-8-azabicyclo[3.2.1]octan-6-carboxylic acid trifluoroacetate (Example 122; 100 mg, 0.19 mmol), N-benzylpiperazine (0.1 ml), triethylamine (0.1 ml, 0.7 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (44 mg, 0.23 mmol) and 4-N,N-dimethylaminopyridine (12 mg, 0.1 mmol)was prepared. The mixture was stirred at room temperature for 20 hours and purified by chromatography on silica gel (dichloromethane:methanol) to give the title compound (102 mg, 85%).

Workup

  1. customwas prepared
  2. custompurified by chromatography on silica gel (dichloromethane:methanol)

Sources & evidence

ORD record
ord-a0f148807c0647f0a590d2d1c5ab725f
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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