Chloroacetaldehyde → HCID 20441341, compound

HRID 1632919Notes

Reaction equation

HRID 1632919 reaction equation
Cl[CH2:2][CH:3]=O.[NH2:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:9]=1.Cl.N>CCOCC.O>[C:17]1([N:10]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:8]3[CH2:7][CH2:6][NH:5][CH2:2][CH2:3][C:9]2=3)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 33Chloroacetaldehyde2×HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 21940715HCID 21940715, compound

Product 1

HCID 20441341HCID 20441341, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

55.6 ml chloroacetaldehyde (45% in water) are added dropwise to 87.2 g 3-(2-aminoethyl)-1-phenylindole, 400 ml 2N hydrochloric acid and 2.5 liters water at 50°. The mixture is heated for 1 hour at 95°, treated once more with 55.6 ml chloroacetaldehyde and heated for a further 45 minutes. The mixture is then cooled to 0°, made alkaline with conc. ammonia and shaken with ether. The organic phase is dried over sodium sulphate, and purified with animal charcoal, and concentrated. The residue 1-chloromethyl-1,2,3,4-tetrahydro-9-phenylpyrido[3,4-b]indole is converted into the hydrochloride, m.p. 174°-180° (from ethanol/ether).

Workup

  1. temperatureThe mixture is heated for 1 hour at 95°
  2. temperatureheated for a further 45 minutes
  3. temperatureThe mixture is then cooled to 0°
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. custompurified with animal charcoal
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9658f0c0ca7d4bc38e0b2d7d46789342
Source dataset
uspto-grants-1984_10
Patent number
US04478750

Reaction notes

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