Triethylamine → HCID 14502148, compound

HRID 704254Notes

Reaction equation

HRID 704254 reaction equation
C([N:3](CC)CC)C.[ClH:8].Cl.[N:10]1([CH2:15][CH:16]([N:18]2[C:31]3[CH:30]=[C:29]([C:32](=[NH:36])OCC)[CH:28]=[CH:27][C:26]=3[S:25][C:24]3[C:19]2=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH3:17])[CH2:14][CH2:13][CH2:12][CH2:11]1>C(O)C>[ClH:8].[N:10]1([CH2:15][CH:16]([N:18]2[C:31]3[CH:30]=[C:29]([C:32]([NH2:36])=[NH:3])[CH:28]=[CH:27][C:26]=3[S:25][C:24]3[C:19]2=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH3:17])[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 14502146HCID 14502146, compound

Product 1

HCID 14502148HCID 14502148, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
25 °C

Procedure

Triethylamine (8.4 cc) is added to a solution of ethyl 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboximidate dihydrochloride (13.63 g) in absolute ethanol (150 cc), and the reaction mixture is diluted with dry ethanol (100 cc). Gaseous ammonia is bubbled for 4 hours into the reaction mixture, which is then stirred for 12 hours at 25° C. The suspension obtained is filtered on sintered glass and the filtrate is concentrated to dryness at 25° C. under reduced pressure (30 mm Hg; 4 kPa) to give a yellow product of meringue-like consistency, which is purified by chromatography on a column of alumina (height: 23 cm; diameter: 4 cm), eluting with mixtures of methylene chloride and methanol in proportions of 95:5 (750 cc) and 50:50 (1,500 cc) and collecting 125-cc fractions. The first 900 cc of eluate are discarded and fractions 8 to 11 are combined and concentrated to dryness at 25° C. under reduced pressure (30 mm Hg; 4 kPa) to give 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamidine hydrochloride (4.5 g) in the form of a yellow product of meringue-like consistency.

Workup

  1. customGaseous ammonia is bubbled for 4 hours into the reaction mixture, which
  2. customThe suspension obtained
  3. filtrationis filtered on sintered glass
  4. concentrationthe filtrate is concentrated to dryness at 25° C. under reduced pressure (30 mm Hg; 4 kPa)
  5. customto give a yellow product of meringue-like consistency, which
  6. customis purified by chromatography on a column of alumina (height: 23 cm; diameter: 4 cm)
  7. washeluting with mixtures of methylene chloride and methanol in proportions of 95:5 (750 cc) and 50:50 (1,500 cc)
  8. customcollecting 125-cc fractions
  9. concentrationconcentrated to dryness at 25° C. under reduced pressure (30 mm Hg; 4 kPa)

Sources & evidence

ORD record
ord-b62eac6129c9499787280386df0a6a20
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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