Ammonia → 5-methoxy-2-nitro-N-[1-(phenylmethyl)-4-piperidinyl]-benzeneacetamide

HRID 1766186Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:13]([O-:15])=[O:14])=[C:7]([CH2:9][C:10]([OH:12])=O)[CH:8]=1.[C:16]1([CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.ClCCl.N>O1CCCC1.C1CCCCC1.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:13]([O-:15])=[O:14])=[C:7]([CH2:9][C:10]([NH:29][CH:26]2[CH2:27][CH2:28][N:23]([CH2:22][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:24][CH2:25]2)=[O:12])[CH:8]=1

Participants

Conditions

Temperature: 40 °C

Procedure

9.24 g (56.98 mmol) of N,N′-carbonyldiimidazole were added to a solution of 12.0 g (56.8 mmol) of 5-methoxy-2-nitrobenzene-acetic acid in 100 ml of tetrahydrofuran and the mixture was stirred for 40 minutes at a reaction temperature of 40° C. After the addition of 11.6 g (56.88 mmol) of 1-(phenylmethyl)-4-piperidineamine the mixture was heated to 40° C. for another hour. The reaction mixture was concentrated by evaporation in vacuo, the solid residue was digested with 50 ml of water and tert.butylmethylether, suction filtered and dried in a circulating air dryer at 50° C. 19.9 g (91% of theoretical) of pale yellow crystals were obtained, Rf 0.6 (eluant: dichloromethane/EE/cyclohexane/methanol/conc. ammonia 300/80/25/25/3 v/v/v/v/v).

Workup

temperaturewas heated to 40° C. for another hour
concentrationThe reaction mixture was concentrated by evaporation in vacuo
filtrationfiltered
customdried in a circulating air dryer at 50° C
custom19.9 g (91% of theoretical) of pale yellow crystals were obtained

Sources & evidence

ORD record: ord-5b31990b39f24e1a8bf95fbb71c29c07
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07230001B1

Reaction notes

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