Sodium Hydroxide → HCID 69956642, compound

HRID 612499Notes

Reaction equation

HRID 612499 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:9]2[CH2:10][C@@H:11]([CH:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:20][CH2:19]3)[O:12][C@@H:13]([CH2:14][NH:15]C=O)[C:8]=2[CH:7]=[CH:6][C:5]=1[O:32][CH3:33].[OH-].[Na+]>Cl.CCO.O>[NH2:15][CH2:14][C@H:13]1[C:8]2[CH:7]=[CH:6][C:5]([O:32][CH3:33])=[C:4]([O:3][CH3:2])[C:9]=2[CH2:10][C@@H:11]([CH:18]2[CH2:19][CH2:20][N:21]([CH2:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:22][CH2:23]2)[O:12]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 86754970HCID 86754970, compound

Product 1

HCID 69956642HCID 69956642, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of cis-N-[3,4-dihydro-5,6-dimethoxy-3-[1-(2-phenylethyl)-4-piperidinyl]-1H-2-benzopyran-1-ylmethyl]formamide hydrochloride (4.7 g, 10 mmol) and its free base (2.1 g, 4.7 mmol) was dissolved in 3N HCl (30 ml)-EtOH (30 ml), and refluxed for 2 h. The reaction was diluted with water, and then stirred and cooled in an ice bath, while 50% aqueous NaOH was added dropwise. A white solid separated from solution and this was collected to afford the titled compound. The compound was recrystallized from toluene to afford the amine as a white solid, mp 100-102° C.

Workup

  1. temperaturerefluxed for 2 h
  2. additionwas added dropwise
  3. customA white solid separated from solution
  4. customthis was collected

Sources & evidence

ORD record
ord-7e3fe3138aed46d38448c2586bc13cd2
Source dataset
uspto-grants-1999_12
Patent number
US06004982

Reaction notes

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