Phenylacetaldehyde → HCID 67158984, compound

HRID 603159Notes

Reaction equation

HRID 603159 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 67158366Benzyl 4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxylate dihydrochloride

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-73ea8a9c8d90464082353b41eb89e413
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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