Phenylacetaldehyde → HCID 52939283, compound

HRID 1841942Notes

Reaction equation

HRID 1841942 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:21])[CH:19]=[CH2:20])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:4][CH2:3]1.[C:22]1([CH2:28][CH:29]=O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:29]([NH:1][CH:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:21])[CH:19]=[CH2:20])=[CH:13][CH:12]=2)(=[O:9])=[O:10])[CH2:4][CH2:3]1)[CH2:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 998PhenylacetaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 52938413HCID 52938413, compound

Product 1

HCID 52939283HCID 52939283, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of N-[4-(4-amino-piperidine-1-sulfonyl)-phenyl]-acrylamide (0.2 g, 3.1 mmol) and phenylacetaldehyde (0.06 ml, 0.52 mmol) in DCE (15 ml) was added triethylamine (0.066 ml, 0.47 mmol) in one portion. The resulting mixture was then stirred at room temperature under a nitrogen atmosphere for 30 minutes, after which time sodium triacetoxy borohydride (0.1 g, 0.47 mmol) was added portion wise. The reaction mixture was stirred at room temperature under a nitrogen atmosphere for a further 2 hours before being concentrated under vacuum. The resulting residue was purified by Prep HPLC to afford the title compound (8 mg, 7% yield) as an off-white powder.

Workup

  1. stirringThe reaction mixture was stirred at room temperature under a nitrogen atmosphere for a further 2 hours
  2. concentrationbefore being concentrated under vacuum
  3. customThe resulting residue was purified by Prep HPLC

Sources & evidence

ORD record
ord-add21eeb0ef1416d862381aa54aafc11
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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