Methanol → HCID 9862105, compound

HRID 612597Notes

Reaction equation

HRID 612597 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]([CH3:7])[CH3:6].O[C:9]1[C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[O:22][CH3:23])[C:14](=[O:24])[C:13]=2[CH:12]=[CH:11][CH:10]=1.Cl[CH2:26]CN(C)C.[CH3:31][OH:32]>ClC1C=CC=CC=1>[CH2:4]([N:5]([CH2:7][CH3:26])[CH2:6][CH2:31][O:32][C:9]1[C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[O:22][CH3:23])[C:14](=[O:24])[C:13]=2[CH:12]=[CH:11][CH:10]=1)[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 79012-Chloro-N,N-dimethylethylamineHCID 820269HCID 820269, compoundHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 9862105HCID 9862105, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Conditions

Temperature
130 °C

Procedure

In a manner similar to Example 2B, prepare the free base of 2 -chloroethyl-dimethylamine hydrochloride (0.60 g, 3.5 mmole). As before, separately prepare a solution of 4-hydroxy-5-methoxy-fluoren-9-one (0.54 g, 2.4 mmole) in methanol (4 mL) and chlorobenzene (12 mL), heating to 130° C. while stirring for 30 minutes. Cool reaction to 100° C. before adding the free base of 2-chloroethyl-dimethylamine prepared previously in 15 mL chlorobenzene. Proceed as before in Example 2B to obtain the title compound as an orange-yellow powder (0.79 g, 91%). m.p. 188-191° C. (dec.).

Workup

  1. temperatureCool
  2. customreaction to 100° C.

Sources & evidence

ORD record
ord-98efedee8ead417887d705d417541e94
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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