Acetic Acid → 3-Chloropropyl 4-(piperidinomethyl)phenyl ether

HRID 33695Notes

Reaction equation

HRID 33695 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 35514794-(3-Chloropropoxy)-benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43659323-Chloropropyl 4-(piperidinomethyl)phenyl ether

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

A solution of the product of Example 11 (5.0 g), piperidine (3.1 mL), and acetic acid (2.0 mL) in DCE (100 mL) was treated with sodium triacetoxyborohydride (9.3 g). After 16 h, the resulting mixture was diluted with water (100 mL) and extracted with DCM (3×50 mL). The combined organic phases were dried (magnesium sulfate) and evaporated, giving the title compound as an amber oil (5.3 g).

Workup

  1. extractionextracted with DCM (3×50 mL)
  2. dry with materialThe combined organic phases were dried (magnesium sulfate)
  3. customevaporated

Sources & evidence

ORD record
ord-0f6a1b78e90f4fbab30ad09c9eb5890a
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Reaction notes

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