1-Piperidinecarboxaldehyde → HCID 57637280, compound

HRID 2078752Notes

Reaction equation

HRID 2078752 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][N:8]([CH3:10])[CH3:9])[S:5][CH:6]=1.C(NC(C)C)(C)C.[Li].[CH:19](N1CCCCC1)=[O:20]>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][N:8]([CH3:10])[CH3:9])[S:5][C:6]=1[CH:19]=[O:20]

Participants

6

Reactant 3

HCID 174291-PiperidinecarboxaldehydeHCID 223495551-(4-Bromothiophen-2-yl)-N,N-dimethylmethanamine2×HCID 45051747Lithium diisopropylamine

Product 1

HCID 57637280HCID 57637280, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To (4-bromo-thiophen-2-ylmethyl)-dimethyl-amine [4.08 g, 18.5 mmol, Intermediate (1)] in tetrahydrofuran (40 mL) at 0° C. and under a nitrogen atmosphere is added Lithium diisopropylamine (2.0M in tetrahydrofuran pentanes from Aldrich chemicals, 20.4 mmol). The orange solution is stirred at 0° C. for 30 minutes. Then N-formylpiperidine is added (2.5 mL, 22.2 mmol). The mixture is allowed to stir at 0° C. for 1 hour. It is diluted with ethyl acetate washed with brine, dried over magnesium sulfate and concentrated. The residual orange oil was chromatographed through silica gel (dichloromethane-1.0M ammonia in methanol, 95:05 as eluant) to produce 3-bromo-5-dimethylaminomethyl-thiophene-2-carbaldehyde [4.4 g, Intermediate (2)] as an orange oil. LC/MS: RT=0.47 minutes, 247.98 m/e (M+H).

Workup

  1. stirringto stir at 0° C. for 1 hour
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residual orange oil was chromatographed through silica gel (dichloromethane-1.0M ammonia in methanol, 95:05 as eluant)

Sources & evidence

ORD record
ord-b6d3ffa60861448ca2cb4483d052ca67
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

Loading…