Methanol → Quinolizidin-2-ylmethyl-2-methoxyindole-3-carboxylate

HRID 741565Notes

Reaction equation

HRID 741565 reaction equation
ClN1[C:6](=[O:7])CCC1=O.[CH2:9]1[CH:18]2[N:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:12][CH2:11][CH:10]1[CH2:19][O:20][C:21]([C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=[O:22].CO>C(Cl)(Cl)Cl>[CH2:9]1[CH:18]2[N:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:12][CH2:11][CH:10]1[CH2:19][O:20][C:21]([C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][C:24]=1[O:7][CH3:6])=[O:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 31398ChlorosuccinimideHCID 131719520Quinolizidin-2-ylmethylindole-3-carboxylate

Product 1

HCID 131719529Quinolizidin-2-ylmethyl-2-methoxyindole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A stirred solution of N-chlorosuccinimide (220 mg, 0.0016 mole) in chloroform (6 ml) at room temperature under nitrogen was treated with a solution of eq-quinolizidin-2-ylmethylindole-3-carboxylate (E9b) (330 mg, 0.0011 mole) in chloroform (6 ml) and stirred for 2 h. The solution was then treated with methanol (0.71 ml, 0.022 mole) and stirring continued. After 3 h a beige precipitate began to form and afar a further 1 h this was filtered off, washed with chloroform,and dried to afford the title compound (E26) as its hydrochloride salt mp 212°-213° C.

Workup

  1. stirringstirring
  2. waitAfter 3 h a beige precipitate began
  3. customto form
  4. waitafar a further 1 h
  5. filtrationthis was filtered off
  6. washwashed with chloroform,and
  7. customdried

Sources & evidence

ORD record
ord-1279c910acfc474caf79b15ed317f30c
Source dataset
uspto-grants-1996_09
Patent number
US05552398

Reaction notes

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