p-Anisoyl chloride → HCID 54596826, compound

HRID 540365Notes

Reaction equation

HRID 540365 reaction equation
[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C@H:7]1[CH2:11][CH2:10][N:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH2:18][NH:17][CH2:16][CH2:15]3)[CH2:8]1.[CH3:22][O:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:22][O:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([N:17]2[CH2:16][CH2:15][C:14]3[C:19](=[CH:20][CH:21]=[C:12]([N:9]4[CH2:10][CH2:11][C@H:7]([N:3]5[CH2:4][CH2:5][CH2:6][C@@H:2]5[CH3:1])[CH2:8]4)[CH:13]=3)[CH2:18]2)=[O:29])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 674693316-((2S,3'S)-2-Methyl-[1,3']bipyrrolidinyl-1'-yl)-1,2,3,4-tetrahydro-isoquinoline

Product 1

HCID 54596826HCID 54596826, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-((2S,3′S)-2-Methyl-[1,3′]bipyrrolidinyl-1′-yl)-1,2,3,4-tetrahydro-isoquinoline in DCM (7 mL) was added 4-Methoxy-benzoyl chloride in DCM, followed by triethylamine. The reaction was quenched with aq. NaHCO3 and DCM work up. The crude product was purified on a silica gel column to obtain the title compound.

Workup

  1. customThe reaction was quenched with aq. NaHCO3 and DCM
  2. customThe crude product was purified on a silica gel column

Sources & evidence

ORD record
ord-532e97e25dc94c44890c5248a02e48a2
Source dataset
uspto-grants-2014_10
Patent number
US08871788B2

Reaction notes

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