Piperidine → 4-{2-(4-piperidin-1-ylmethyl-piperidin-1-yl)-benzyl}-morpholine

HRID 1179356Notes

Reaction equation

HRID 1179356 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]2[CH2:19][CH2:18][CH:17]([CH:20]=O)[CH2:16][CH2:15]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[K+]>ClC(Cl)C>[N:22]1([CH2:20][CH:17]2[CH2:18][CH2:19][N:14]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[CH2:15][CH2:16]2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 14797Potassium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 58978046HCID 58978046, compound

Product 1

HCID 100439024-{2-(4-piperidin-1-ylmethyl-piperidin-1-yl)-benzyl}-morpholine

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of the product of Example 17 (288 mg) and piperidine (0.12 mL) in dichloroethane (DCE, 2 mL) was treated with sodium triacetoxyborohydride (297 mg). After 16 h, the resulting mixture was treated with 10% potassium hydroxide (2 mL), and extracted with DCM (2×2 mL). The combined extracts were dried (MgSO4), and chromatographed on silica gel (0-8% 2 M methanolic ammonia/DCM), giving the title compound as a colorless oil (100 mg).

Workup

  1. extractionextracted with DCM (2×2 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customchromatographed on silica gel (0-8% 2 M methanolic ammonia/DCM)

Sources & evidence

ORD record
ord-ecf25f6be0114d04995767e250578e7a
Source dataset
uspto-grants-2007_10
Patent number
US07279491B2

Reaction notes

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