1-Methylpiperazine → (4-Methyl-1-piperazinyl)[tetrahydro-4-(4-methoxyphenyl)-2H-pyran-4-yl]methanone

HRID 273001Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15]([OH:17])=O)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([C:15]([N:22]3[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]3)=[O:17])[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)=[CH:7][CH:8]=1

Participants

Reactant 3

HCID 531671-Methylpiperazine

HCID 9698024-(4-Methoxyphenyl)oxane-4-carboxylic acid

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 16415282(4-Methyl-1-piperazinyl)[tetrahydro-4-(4-methoxyphenyl)-2H-pyran-4-yl]methanoneYield 77%

Procedure

The title compound (515 mg, 77%) was prepared using 4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-carboxylic acid, N-methyl-piperazine and O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) similarly to the procedure used for example 166. HRMS ESI+ m/z 319.2009 [MH]+.

Sources & evidence

ORD record: ord-76d1df7f3b9b4e92979aff2e83536585
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456164B2

Reaction notes

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