3,5-Difluorobenzaldehyde → Carbamic acid, [1-[(3,5-difluorophenyl)methyl]-4-piperidinyl]-, 1,1-dimethylethyl ester

HRID 1432193Notes

Reaction equation

HRID 1432193 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([F:24])[CH:23]=1)[CH:19]=O>>[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([F:24])[CH:23]=1)[CH2:19][N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 5881603,5-DifluorobenzaldehydeHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 22182435Carbamic acid, [1-[(3,5-difluorophenyl)methyl]-4-piperidinyl]-, 1,1-dimethylethyl ester

Procedure

The title compound was prepared (3.3 g, 100%) from tert-butyl piperidin-4-ylcarbamate (2 g, 10 m mol) and 3,5-difluorobenzaldehyde (1.42 g, 10 mmol) by following the general procedure described for Preparation 3. 1H NMR (400 MHz, CDCl3): δ 6.85 (m, 2H), 6.65 (m, 1H), 4.45 (bs, 1H), 3.50 (m, 1H), 3.05 (s, 2H), 2.75 (m, 2H), 2.10 (m, 2H), 1.90 (m, 2H), 1.45 (m, 11H). MS (ESI) m/z: Calculated: 326.38; Observed: 327.0 (M++1).

Workup

  1. customdescribed for Preparation 3

Sources & evidence

ORD record
ord-d66514a30fa746deba1c948ccdb157cd
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

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