Thiomorpholine → HCID 178451268, compound

HRID 2063233Notes

Reaction equation

HRID 2063233 reaction equation
[C:1]([CH:8]([NH2:12])[CH2:9][CH2:10]Br)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH:13]1[CH2:18][CH2:17][S:16][CH2:15][CH2:14]1>C(Cl)Cl>[C:1]([CH:8]([NH2:12])[CH2:9][CH2:10][SH:16]1[CH2:17][CH2:18][NH:13][CH2:14][CH2:15]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 14193053HCID 14193053, compound

Product 1

HCID 178451268HCID 178451268, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-BOC-aminopropyl bromide (3.07 g; 12.9 mmol) and thiamorpholine (2.6 mL; 25.8 mmol) in CH2Cl2 (25 mL) is heated at the reflux temperature for 24 h. The mixture is cooled at r.t., filtered, washed with water (2×50 mL), dried over Na2SO4 and evaporated to dryness in vacuum. Purification by flash chromatography on silica gel (eluent CHCl3/CH3OH 9:1) yields 1-(3-BOC-aminopropyl)-thiamorpholine (3.1 g; 11.96 mmol), as a transparent oil.

Workup

  1. filtrationfiltered
  2. washwashed with water (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness in vacuum
  5. customPurification by flash chromatography on silica gel (eluent CHCl3/CH3OH 9:1)

Sources & evidence

ORD record
ord-88da4883808b4f1f9d8cc50980b45c7a
Source dataset
uspto-grants-2012_10
Patent number
US08288368B2

Reaction notes

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