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

HRID 456939
Notes
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Reaction equation

HRID 456939 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 11
1,2-Dichloroethane
Solvent
HCID 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-d3819a0f4ecc4f77837417e325b4ef5c
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07186732B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes