Phenylacetaldehyde → HCID 67158984, compound

HRID 2371117Notes

Reaction equation

HRID 2371117 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[CH2:12][CH2:11]2)[CH2:4]1.C(N(CC)C(C)C)(C)C.[C:35]1([CH2:41][CH:42]=O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.S([O-])([O-])(=O)=O.[Mg+2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[C:35]1([CH:41]([N:3]2[CH2:8][CH2:7][CH2:6][C@H:5]([CH2:9][N:10]3[CH2:11][CH2:12][N:13]([C:16]([O:18][CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[O:17])[CH2:14][CH2:15]3)[CH2:4]2)[CH3:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 5

HCID 998PhenylacetaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 67158366HCID 67158366, compound

Product 1

HCID 67158984HCID 67158984, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl 4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxylate dihydrochloride (1.5 g) was suspended in THF (45 ml) and stirred at room temperature. N,N-Diisopropylethylamine (3.3 ml) was added followed by phenylacetaldehyde (0.9 ml) and magnesium sulphate (300 mg). After 20 minutes sodium triacetoxyborohydride (1.6 g) was added and stirring continued overnight. Inorganic residues were removed by filtration and the filtrate was adsorbed onto silica for purification by chromatography eluting with 0-7% methanol/dichloromethane. This gave benzyl 4-{[(3R)-1-phenylethylpiperidin-3-yl]methyl}piperazine-1-carboxylate as a pale yellow gum (960 mg).

Workup

  1. stirringstirring continued overnight
  2. customInorganic residues were removed by filtration
  3. customthe filtrate was adsorbed onto silica for purification by chromatography
  4. washeluting with 0-7% methanol/dichloromethane

Sources & evidence

ORD record
ord-8bff262082a74b1aa380cd1b4661dc72
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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