Trifluoroacetic acid → 3-Bromo-5-(((4-phenylpiperidin-4-yl)methoxy)methyl)pyridine

HRID 656518Notes

Reaction equation

HRID 656518 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][CH2:10][C:11]2([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)[CH:5]=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][O:9][CH2:10][C:11]2([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57557588Tert-butyl 4-(((5-bromopryidin-3-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate

Product 1

HCID 248009253-Bromo-5-(((4-phenylpiperidin-4-yl)methoxy)methyl)pyridineYield 112.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(((5-bromopryidin-3-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (100 mg, 0.2 mmoL) in methylene chloride (2 mL) was treated with TFA (0.5 mL). After 1 h, the reaction was concentrated, and the resulting residue was evaporated from methylene chloride (2×). Preparative HPLC afforded 88.0 mg (92%) of the desired compound as its TFA salt. 1H-NMR (CDCl3, 400 MHz) δ 8.65 (s, 1H), 8.52 (s, 1H), 7.84 (s, 1H), 7.24-7.43 (m, 5H), 6.85 (s, br, 1H), 4.46 (s, 2H), 3.45 (s, 2H), 3.33-3.38 (m, 2H), 2.91-2.95 (m, 2H), 2.43-2.48 (m, 2H), 2.22-2.30 (m, 2H). Mass spec.: 362.99 (MH)+.

Workup

  1. concentrationthe reaction was concentrated
  2. customthe resulting residue was evaporated from methylene chloride (2×)

Sources & evidence

ORD record
ord-29bfde726d0641d98eac599121136b2d
Source dataset
uspto-grants-2011_12
Patent number
US08071778B2

Reaction notes

Loading…