Phenylacetaldehyde → n-(3,4-Dichlorophenyl)-4-{[4-(2-phenylethyl)morpholin-2-yl]carbonyl}piperazine-1-carboxamide

HRID 2371199Notes

Reaction equation

HRID 2371199 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([CH:20]3[O:25][CH2:24][CH2:23][NH:22][CH2:21]3)=[O:19])[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH:33]=O)=[CH:28][CH:27]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([CH:20]3[O:25][CH2:24][CH2:23][N:22]([CH2:33][CH2:32][C:29]4[CH:30]=[CH:31][CH:26]=[CH:27][CH:28]=4)[CH2:21]3)=[O:19])[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 998PhenylacetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 57656890N-(3,4-Dichlorophenyl)-4-(morpholin-2-ylcarbonyl)piperazine-1-carboxamide

Product 1

HCID 57656741n-(3,4-Dichlorophenyl)-4-{[4-(2-phenylethyl)morpholin-2-yl]carbonyl}piperazine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(3,4-dichlorophenyl)-4-(morpholin-2-ylcarbonyl)piperazine-1-carboxamide (350 mg) in dichloromethane (10 ml) under an argon atmosphere was added phenacetaldehyde (0.16 mL) then NaBH(OAc)3 (383 mg) and the reaction was stirred for 3.5 h. The solvent was then removed under reduced pressure and dissolved in dichloromethane (40 ml) and 1M NaOH (20 ml). The organic layer was separated, dried (MgSO4) and evaporated. Purification by column chromatography 3-7% MeOH:DCM afforded the title compound (170 mg) as a white foam.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. dissolutiondissolved in dichloromethane (40 ml)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customPurification by column chromatography 3-7% MeOH

Sources & evidence

ORD record
ord-0db5b85e350c47c8a928824c6e00c226
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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