Formaldehyde → 2-Chloro-10-[4-(1-pyrrolidinyl)-2-butynyl]phenothiazine

HRID 462080Notes

Reaction equation

HRID 462080 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:16][C:17]#[CH:18])[C:4]=2[CH:3]=1.[CH2:19]=O.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>O1CCOCC1>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:16][C:17]#[C:18][CH2:19][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 149596962-Chloro-10-propargylphenothiazine

Product 1

HCID 213904902-Chloro-10-[4-(1-pyrrolidinyl)-2-butynyl]phenothiazine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Following the procedure given in Example 1B, 2-chloro-10-propargylphenothiazine (21.7 g.; 0.08 mole) was caused to react with 3.8 g of paraformaldehyde and 7.1 g. (0.1 mole) of pyrrolidine in the presence of a trace of cuprous chloride in dioxane. Recrystallized from ether-hexane, the pure 2-chloro-10-[4-(1-pyrrolidinyl)-2-butynyl]-phenothiazine thus obtained melted at 48.0°-50.0° C.

Workup

  1. customRecrystallized from ether-hexane

Sources & evidence

ORD record
ord-f4063b9546c647f9ad2e9670c7ee508a
Source dataset
uspto-grants-1977_12
Patent number
US04065471

Reaction notes

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