Benzylamine → HCID 59730151, compound

HRID 228193Notes

Reaction equation

HRID 228193 reaction equation
[CH:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)=O.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[BH4-].[Na+]>CO>[CH2:19]([NH:26][CH2:1][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 4311764Sodium borohydrideHCID 28825277HCID 28825277, compound

Product 1

HCID 59730151HCID 59730151, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 4-(4-Formyl-phenoxy)-benzamide from Example 247, step 2 (0.1 g, 0.41 mmol), benzylamine (0.040 g, 0.38 mmol), 4 Å molecular sieves (1 g) in methanol (5 mL), and stir for 18 h at ambient temperature. Add sodium borohydride (0.058 g, 1.52 mmol), agitate 66 h at ambient temperature. Filter through a 5 g SCX column, eluting first with 1:1 dichloromethane/methanol. Discard the first washings, then elute with 1:1 dichloromethane/2 M ammonia in methanol. Collect the eluants and concentrate in vacuo. Purify by Chromatotron, on a 2 mm silica plate, eluting with 90:10:1 dichloromethane/ethanol/ammonium hydroxide to afford the title compound (0.058 g, 46%): mass spectrum (ion spray): m/z=333.06 (M+1); 1H NMR (DMSO-d6): 7.82 (m, 3H), 7.39-7.18 (m, 5H), 7.02-6.97 (m, 4H), 3.67-3.66 (2s, 4H).

Workup

  1. filtrationFilter through a 5 g SCX column
  2. washeluting first with 1:1 dichloromethane/methanol
  3. washelute with 1:1 dichloromethane/2 M ammonia in methanol
  4. customCollect the eluants
  5. concentrationconcentrate in vacuo
  6. customPurify by Chromatotron, on a 2 mm silica plate
  7. washeluting with 90:10:1 dichloromethane/ethanol/ammonium hydroxide

Sources & evidence

ORD record
ord-4808992f0aa24fae92c6fa4bcb78d9f9
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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