Piperidine → HCID 59577773, compound

HRID 1947522Notes

Reaction equation

HRID 1947522 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:19]=[C:18]2[C:14]([CH:15]=[C:16]([CH:20]=O)[NH:17]2)=[CH:13][CH:12]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[N:22]1([CH2:20][C:16]2[NH:17][C:18]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[C:11]([O:10][C:2]2[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=2)[CH:19]=3)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 59577683HCID 59577683, compound

Product 1

HCID 59577773HCID 59577773, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 6-(benzothiazol-2-yloxy)-1H-indole-2-carbaldehyde (47 mg, 0.16 mmol) in DCM (3 mL) was added piperidine (0.14 mL, 0.12 g, 0.48 mmol), Na(OAc)3BH (51 mg, 0.24 mmol) and the reaction mixture was stirred (rt, 12 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):DCM (0-8%) to provide the title compound as a yellow solid (18 mg, 31%). MS (ESI): mass calcd. for C21H21N3OS, 363.1; m/z found, 364.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.80 (s, 1H), 7.76-7.71 (m, 1H), 7.62 (dd, J=7.9, 0.7, 1H), 7.54 (d, J=8.5, 1H), 7.41-7.33 (m, 1H), 7.30 (d, J=2.0, 1H), 7.25-7.20 (m, 1H), 7.04 (dd, J=8.5, 2.2, 1H), 6.34 (d, J=1.0, 1H), 3.61 (s, J=5.4, 2H), 2.62-2.26 (m, 4H), 1.72-1.53 (m, J=10.9, 5.6, 4H), 1.54-1.30 (m, J=5.1, 2H).

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-8c7a8cac112846928642520d5d1db9e5
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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