Formaldehyde → 3-(4-Bromo-phenyl)-1-methyl-piperidin-3-ol

HRID 1505919Notes

Reaction equation

HRID 1505919 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)([OH:14])[CH2:9]1)=O)(C)(C)C.C=O>C(O)=O>[Br:21][C:18]1[CH:17]=[CH:16][C:15]([C:10]2([OH:14])[CH2:11][CH2:12][CH2:13][N:8]([CH3:6])[CH2:9]2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 58266476Tert-butyl 3-(4-bromophenyl)-3-hydroxypiperidine-1-carboxylate

Product 1

HCID 582664783-(4-Bromo-phenyl)-1-methyl-piperidin-3-olYield 93%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-(4-bromo-phenyl)-3-hydroxypiperidine-1-carboxylic acid tert-butyl ester (1.39 g, 3.9 mmol), formic acid (18.4 mL) and formaldehyde (1.6 mL) was heated under microwave irradiation at 150° C. for 5 minutes. The cooled reaction mixture was loaded onto a 70 g SCX-2 cartridge which was washed with methanol (200 mL) and then eluted with 2N ammonia in methanol (200 mL). Concentration of the combined basic fractions in vacuo afforded the title compound (978 mg, 93%) as a brown oil. LCMS (Method B): RT=1.84 min, M+H+=270.

Workup

  1. customThe cooled reaction mixture
  2. washwas washed with methanol (200 mL)
  3. washeluted with 2N ammonia in methanol (200 mL)

Sources & evidence

ORD record
ord-397ea370f54244a7a0c090408496f1e3
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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