Sulfuric Acid → 2-(1-Diphenylmethylpiperidine-4-yl)-ethylamine

HRID 1280774Notes

Reaction equation

[Na].[C:2]1([CH:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][C:16]#[N:17])[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[OH-].[Na+]>C1COCC1>[C:2]1([CH:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][NH2:17])[CH2:11][CH2:10]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2.2 g (58.2 mmol) sodium borohydroxide are suspended in 50 ml abs. THF and cooled to ca. 0° C. under moisture exclusion. 6.7 g (23.1 mmol) (1-diphenylmethylpiperidin-4-yl)-acetonitrile are added and the mixture is subsequently cooled to −5° C. to −10° C. and added dropwise to 1.5 ml (26.7 mmol) 95% sulfuric acid (vigorous foaming). The suspension is left to stand for two days at RT without further cooling. Under renewed cooling to ca. 0° C., 40 ml 2 M sodium hydroxide solution is added dropwise. The aqueous phase is extracted with 30 ml THF and thereafter the combined organic phases are washed twice, each with 30 ml saturated NaCl solution, dried over sodium sulfate and the solution is removed under vacuum. The residue is chromatographically purified over silica gel with CHCl3/CH3OH/N4OH (90/10/1). Yield: 3.9 g (57%).

Workup

temperaturethe mixture is subsequently cooled to −5° C. to −10° C.
waitThe suspension is left
extractionThe aqueous phase is extracted with 30 ml THF
washthe combined organic phases are washed twice
dry with materialeach with 30 ml saturated NaCl solution, dried over sodium sulfate
customthe solution is removed under vacuum
customThe residue is chromatographically purified over silica gel with CHCl3/CH3OH/N4OH (90/10/1)

Sources & evidence

ORD record: ord-d35ac7b4e4d0412ebd39b994fbf7ebc7
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451816B1

Reaction notes

Loading…