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Triethylamine → N-(2-(4-bromophenyl)propan-2-yl)-2-(quinuclidin-3-yl)acetamide

HRID 2281250
Notes
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Reaction equation

HRID 2281250 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([CH2:10][C:11]([OH:13])=O)[CH2:3]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]([NH2:48])([CH3:47])[CH3:46])=[CH:41][CH:40]=1.C(N(CC)CC)C>CN(C=O)C>[Br:38][C:39]1[CH:40]=[CH:41][C:42]([C:45]([NH:48][C:11](=[O:13])[CH2:10][CH:4]2[CH:5]3[CH2:6][CH2:7][N:2]([CH2:9][CH2:8]3)[CH2:3]2)([CH3:46])[CH3:47])=[CH:43][CH:44]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 230091162-(4-Bromophenyl)propan-2-amineHCID 230241472-(Quinuclidin-3-yl)acetic acid hydrochloride

Product 1

HCID 68327949N-(2-(4-bromophenyl)propan-2-yl)-2-(quinuclidin-3-yl)acetamide
Yield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(quinuclidin-3-yl)acetic acid hydrochloride (0.97 g, 4.7 mmol) in DMF (30 mL) was added HATU (1.79 g, 4.72 mmol), 2-(4-bromophenyl)propan-2-amine (1.0 g, 4.7 mmol), and triethylamine (3.9 mL, 28 mmol). The resulting mixture was stirred at 60° C. for 16 h. The mixture was concentrated in vacuo, diluted with EtOAc and washed with brine. The organic layer was dried over Na2SO4 and evaporated to afford crude product, which was purified by silica gel column chromatography (EtOAc/methanol 50/1 to 3/1) to obtain N-(2-(4-bromophenyl)propan-2-yl)-2-(quinuclidin-3-yl)acetamide as a yellow solid (1.3 g, 76%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with EtOAc
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated
  6. customto afford crude product, which
  7. customwas purified by silica gel column chromatography (EtOAc/methanol 50/1 to 3/1)

Sources & evidence

ORD record
ord-15844f54be8346cc81bc8d0aaeb2204f
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09139580B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes