Sodium Hydroxide → HCID 10498076, compound

HRID 1741594Notes

Reaction equation

HRID 1741594 reaction equation
[S:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[CH:3]=[CH:2]1.[C:10]([N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24]I)[CH2:19][CH2:18]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[OH-].[Na+]>C(Cl)Cl>[C:10]([N:17]1[CH2:18][CH2:19][CH:20]([CH2:23][CH2:24][N:6]2[CH2:7][CH2:8][C:9]3[S:1][CH:2]=[CH:3][C:4]=3[CH2:5]2)[CH2:21][CH2:22]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 30850764,5,6,7-Tetrahydrothieno(3,2-c)pyridineHCID 9974426Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate

Product 1

HCID 10498076HCID 10498076, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine.HCL (2-1) (1.76 g, 0.01 moles) in CH2Cl2 (15 ml) was treated with 2-(N-BOC-4-piperidinyl)ethyl iodide (2--2) (3.73 g, 0.011 moles) followed by 20% NaOH (10 ml) and Aliquot-336 (Aldrich). After stirring for 20 hours the reaction mixture was diluted with CH2Cl2 and the organic phase was separated, washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography on silica gel eluting with CHCl3 (98)/MeOH(2) to give pure 2-3.

Workup

  1. customthe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel eluting with CHCl3 (98)/MeOH(2)
  6. customto give pure 2-3

Sources & evidence

ORD record
ord-48f1ed848e924dbdbacdb71eb84b6891
Source dataset
uspto-grants-1994_08
Patent number
US05334596

Reaction notes

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