Sodium Hydroxide → HCID 23507360, compound

HRID 2380975Notes

Reaction equation

[BH4-].[Na+].[C:3]1([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:25]=[CH:24][C:19]([NH:20][N+]([O-])=O)=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[C:3]1([N:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([NH2:20])=[CH:24][CH:25]=3)[CH2:13][CH2:14]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of sodium borohydride (63 mg, 1.68 mmol) in ethanol (1 ml) was added drop-wise to a stirred solution of 4-(4-phenylpiperazine-1-yl methyl)-nitro-aniline (1 g, 3.36 mmol) and tin (II) dichloride dihydrate (2.27 g, 10.10 mmol) in ethanol (20 ml) at 60° C. The resulting solution was stirred for 2 h after which the reaction was cooled to 0° C. and basified (pH>10) by the addition of sodium hydroxide (2M). The aqueous layer was extracted with dichloromethane (3×20 ml) and the combined organics washed with brine, then dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (hexanes/ethyl acetate 1:1) to afford the title compound as a pale yellow solid (441 mg, 49%). HPLC retention time 5.82 min. Mass spectrum (ES+) m/z 268 (M+H).

Workup

extractionThe aqueous layer was extracted with dichloromethane (3×20 ml)
washthe combined organics washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (hexanes/ethyl acetate 1:1)

Sources & evidence

ORD record: ord-f3d85a7b268e400bb9b2a549a352bacc
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258138B2

Reaction notes

Loading…