Hippuric Acid → 1-(4-Chlorobenzyl)piperidine

HRID 1280995Notes

Reaction equation

HRID 1280995 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10](CNCC(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C(O)(=O)CNC(C1C=CC=CC=1)=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 464Hippuric AcidHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 184261581-(4-chlorobenzyl)-4-{N-(2,2-diphenylethyl)aminomethyl}piperidine

Product 1

HCID 45457851-(4-Chlorobenzyl)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 1-(4-chlorobenzyl)-4-{N-(2,2-diphenylethyl)aminomethyl}piperidine (0.084 mmol) in CH2Cl2 was treated with hippuric acid (1.1 equiv.), HBTU (1.1 equiv.), HOBt (1.1 equiv.). The reaction mixture was stirred at 40° C. for 24 h. General workup and preparative TLC (SiO2) afforded 4-{N-(N-benzoylglycyl)-N-(2,2-diphenylethyl)aminomethyl)}-1-(4-chlorobenzyl)piperidine (Compound No. 524) (8.5 mg, 17%): The purity was determined by RPLC/MS (98%); ESI/MS m/e 580 (M++H, C36H38ClN3O2).

Sources & evidence

ORD record
ord-d80c5881f68444ae86c8ae0c1261bed3
Source dataset
uspto-grants-2002_09
Patent number
US06451842B1

Reaction notes

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