Piperidine → HCID 49832492, compound

HRID 1947520Notes

Reaction equation

HRID 1947520 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][CH3:21])[C:15]([CH:22]=O)=[CH:14]2.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:20]([N:16]1[C:17]2[C:13](=[CH:12][C:11]([O:10][C:2]3[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)=[CH:19][CH:18]=2)[CH:14]=[C:15]1[CH2:22][N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[CH3:21]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 59577472HCID 59577472, compound

Product 1

HCID 49832492HCID 49832492, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of 5-(benzothiazol-2-yloxy)-1-ethyl-1H-indole-2-carbaldehyde (100 mg, 0.3 mmol) in DCE (3 mL) was added piperidine (0.06 mL, 51 mg, 0.62 mmol), Na(OAc)3BH (131 mg, 0.62 mmol) and the reaction mixture was stirred (rt, 60 h). The reaction mixture was partitioned between saturated NaHCO3 (10 ml) and DCM (20 mL). The organic layer was separated and the aqueous layer was extracted with DCM (2×25 mL). The organic layer was dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using MeOH (0.2 M NH3):DCM (0-8%) to provide the title compound as a yellow solid (82 mg, 68%). MS (ESI): mass calcd. for C23H25N3OS, 391.2; m/z found, 392.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.73 (d, J=8.1, 1H), 7.59 (d, J=7.9, 1H), 7.49 (d, J=2.3, 1H), 7.39-7.29 (m, 2H), 7.23 (d, J=13.2, 1H), 7.12 (dd, J=8.8, 2.4, 1H), 6.35 (s, 1H), 4.36-4.21 (m, 2H), 3.56 (s, 2H), 2.49-2.25 (m, 4H), 1.54 (d, J=5.3, 4H), 1.51-1.32 (m, 5H).

Workup

  1. customThe reaction mixture was partitioned between saturated NaHCO3 (10 ml) and DCM (20 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with DCM (2×25 mL)
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-97b702f7c829473b834365046e296f16
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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