4-Fluoroaniline → Benzyl 4-(((4-fluorophenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate

HRID 2036097Notes

Reaction equation

[O:1]1[C:3]2([CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:10])[CH2:5][CH2:4]2)[CH2:2]1.[F:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1.Cl([O-])(=O)(=O)=O.[Li+]>>[F:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][CH2:2][C:3]2([OH:1])[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:10])[CH2:5][CH2:4]2)=[CH:22][CH:21]=1

Participants

Reactant 3

HCID 97314-Fluoroaniline

HCID 13016598Benzyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

HCID 23665649Lithium perchlorate

Product 1

HCID 56773849Benzyl 4-(((4-fluorophenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate

Procedure

The object product (2.8 g, 98%) was obtained in the same manner as in Example 24(1) and using benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (1.98 g), 4-fluoroaniline (889 mg) and lithium perchlorate (960 mg).

Sources & evidence

ORD record: ord-21db5bbe6f67459692392a7159629800
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575167B2

Reaction notes

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