Acetaldehyde → HCID 57656892, compound

HRID 2371184Notes

Reaction equation

HRID 2371184 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]3[CH2:24][NH:23][CH2:22][CH2:21][N:20]3[C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:35](=O)[CH3:36].ClC1C=C(NC(N2CCN(C[C@@H]3OCCN(CCC4C=NC=CC=4)C3)CC2)=O)C=CC=1Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH:19]3[CH2:24][N:23]([CH2:35][CH3:36])[CH2:22][CH2:21][N:20]3[C:25]([O:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:26])[CH2:16][CH2:17]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 3

HCID 177AcetaldehydeHCID 57656754HCID 57656754, compoundHCID 57656834HCID 57656834, compound

Product 1

HCID 57656892HCID 57656892, compoundYield 18%

Procedure

Benzyl 2-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)methyl]piperazine-1-carboxylate and acetaldehyde were used in a similar manner to N-(3,4-dichlorophenyl)-4-{[(25)-4-(2-pyridin-3-ylethyl)morpholin-2-yl]methyl}piperazine-1-carboxamide, except that after purification of the residue on a Redisep® silica column, eluting with ethyl acetate/MeOH (30:70), the solid, after precipitation from CH2Cl2 with isohexane, was further purified on an SCX column, eluting sequentially with ethyl acetate, MeOH and 1% ammonia/MeOH to give the title product (20 mg, 18%).

Workup

  1. customexcept that after purification of the residue on a Redisep® silica column
  2. washeluting with ethyl acetate/MeOH (30:70)
  3. customthe solid, after precipitation from CH2Cl2 with isohexane
  4. customwas further purified on an SCX column
  5. washeluting sequentially with ethyl acetate, MeOH and 1% ammonia/MeOH

Sources & evidence

ORD record
ord-7ad8e8300e0d443aac75e507ca4eff5b
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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