Phenethylamine → HCID 44434943, compound

HRID 228488Notes

Reaction equation

HRID 228488 reaction equation
[N:1]1([C:7]([C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=3)=[N:13][CH:14]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.COC(OC)OC.[CH2:31]([NH2:39])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[BH4-].[Na+]>CO>[NH3:1].[CH3:7][OH:8].[CH2:31]([NH:39][CH2:20][C:19]1[CH:22]=[CH:23][C:16]([O:15][C:12]2[N:13]=[CH:14][C:9]([C:7]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:8])=[CH:10][CH:11]=2)=[CH:17][CH:18]=1)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 1001PhenethylamineHCID 9005Trimethyl orthoformateHCID 4311764Sodium borohydrideHCID 59729964HCID 59729964, compound

Product 2

HCID 21705897Ammonia methanolHCID 44434943HCID 44434943, compoundYield 151.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 4-[5-(Piperidine-1-carbonyl)-pyridin-2-yloxy]-benzaldehyde (72.0 mg, 0.23 mmol), MeOH (2.3 mL), Trimethylorthoformate (1.6 mL), and Phenethylamine (26 uL, 0.21 mmol). After the reaction stirs for 72 hours at room temperature under a Nitrogen atmosphere, add NaBH4 (10.5 mg, 0.28 mmol). After 5 hours, concentrate the reaction under reduced pressure and add the mixture to a 2 g SCX column. Wash with MeOH and then 1N NH3 MeOH to afford 72.2 mg (75% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 1.5-1.8 (6H, m), 2.8-3.0 (4H, m), 3.3-3.8 (4H, m), 3.85 (2H, s), 6.8 (1H, d), 7.1-7.4 (9H, m), 8.0 (1H, d), 8.2 (1H, s); MS m/z 416 (M+1).

Workup

  1. waitAfter 5 hours
  2. concentrationconcentrate
  3. customthe reaction under reduced pressure
  4. additionadd the mixture to a 2 g SCX column
  5. washWash with MeOH

Sources & evidence

ORD record
ord-7f841324f1954e2da780606a6f61a508
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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