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Acetic Acid → 4-[{N-(2-amino-5-chlorobenzoyl)glycyl}aminomethyl]-1-(4-ethoxybenzyl)piperidine

HRID 279323
Notes
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Reaction equation

HRID 279323 reaction equation
C([BH3-])#N.[Na+].[NH2:5][C:6]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:7]=1[C:8]([NH:10][CH2:11][C:12]([NH:14][CH2:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[O:13])=[O:9].[CH2:27]([O:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1)[CH3:28].C(O)(=O)C>CO>[NH2:5][C:6]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:7]=1[C:8]([NH:10][CH2:11][C:12]([NH:14][CH2:15][CH:16]1[CH2:17][CH2:18][N:19]([CH2:34][C:33]2[CH:36]=[CH:37][C:30]([O:29][CH2:27][CH3:28])=[CH:31][CH:32]=2)[CH2:20][CH2:21]1)=[O:13])=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 248344-EthoxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 184262164-[{N-(2-amino5-chlorobenzoyl)glycyl}aminomethyl]piperidine

Product 1

HCID 184261294-[{N-(2-amino-5-chlorobenzoyl)glycyl}aminomethyl]-1-(4-ethoxybenzyl)piperidine

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent
2×

Conditions

Temperature
60 °C

Procedure

Sodium cyanoborohydride (140 mmol) in methanol (0.4 mL) was added to a mixture of 4-[(N-(2-amino-5-chlorobenzoyl)glycyl)aminomethyl]piperidine (0.10 mmol), 4-ethoxybenzaldehyde (0.10 mmol), acetic acid (0.050 mL), and methanol (1.6 mL). The reaction mixture was stirred at 60° C. for 14 h. The reaction mixture was loaded onto Varian™ SCX column and washed with CH3OH (20 mL). Product was eluted using 2 N NH3 in CH3OH (6 mL) and concentrated. Preparative TLC (SiO2, AcOEt/CH3OH 5:1) afforded 4-[{N-(2-amino-5-chlorobenzoyl)glycyl}aminomethyl]-1-(4-ethoxybenzyl)piperidine (Compound No. 1429) and 1-(4-ethoxybenzyl)-4-[{N-(2-(4-ethoxybenzyl)amino-5-chlorobenzoyl)glycyl)aminomethyl]piperidine (Compound No. 1433).

Workup

  1. washwashed with CH3OH (20 mL)
  2. washProduct was eluted
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-240e1e92bcba4ddd8befbfad2c8266a9
Source dataset
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06362177B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes