4-Nitrophenol → 4-(1-Methylpiperidin-3-ylmethoxy)-phenylamine

HRID 2105304Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-])=O.Cl[CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][N:15]([CH3:19])[CH2:14]1>>[CH3:19][N:15]1[CH2:16][CH2:17][CH2:18][CH:13]([CH2:12][O:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:14]1

Participants

Reactant 2

HCID 9804-Nitrophenol

HCID 1036743-(Chloromethyl)-1-methylpiperidine

Product 1

HCID 219747984-(1-Methylpiperidin-3-ylmethoxy)-phenylamine

Procedure

Using the procedure of Example 56, 4-nitro-phenol Compound 104a was used in place of Compound 36a and 3-chloromethyl-1-methyl-piperidine Compound 104b was used in place of Compound 56a and carried forward to provide 4-(1-methyl-piperidin-3-ylmethoxy)-phenylamine Compound 104d. MS 221 (MH+). Using the procedure of Example 1, 5-(2,4-dichloro-phenyl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,6,8-tetraaza-acenaphthylene-2-carboxylic acid Compound 43c was used in place of Compound 1 and Compound 104d was used in place of 4-piperidin-1-ylmethyl-phenylamine Compound 1k to give Compound 32. MS 583, 585, 587 (MH+).

Sources & evidence

ORD record: ord-a8545058cabc466783da993ca6b580ea
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579356B2

Reaction notes

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