Chloroform → HCID 21402909, compound

HRID 972960Notes

Reaction equation

HRID 972960 reaction equation
[CH:1]([NH:3][CH2:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][C:8]2[CH:16]=[CH:17][CH:18]=[CH:19][C:7]=2[CH2:6]1)=O.[OH-].[Na+].C(Cl)(Cl)Cl>O.C1C=CC=CC=1>[CH2:4]1[CH:5]2[CH2:6][C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[CH2:9][C:10]3[C:11]2=[C:12]([CH:13]=[CH:14][CH:15]=3)[CH:1]=[N:3]1

Participants

6

Reactant 3

HCID 6212Chloroform3×HCID 14798Sodium HydroxideHCID 21402950HCID 21402950, compound

Product 1

HCID 21402909HCID 21402909, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

N-Formyl-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-10-methylamine (6.7 g, 0.027 mole), described in Example 334, in combined with polyphosphoric acid (50 g) and the mixture stirred for 3.5 hr. at 155° - 160° C. (bath temperature). The darkish reaction mixture is poured hot into stirred ice-water (400 ml). After stirring for 0.5 hr. (and treatment of the sticky precipitate with a glass rod) a solution of sodium hydroxide (60 g) in water is added, followed by chloroform. The chloroform solution is twice replaced by fresh chloroform and after 1 hr. the precipitate is almost dissolved. The combined chloroform solutions are washed with water, dried (Na2SO4) and taken to dryness to give a dark residue. The residue is dissolved in a little benzene and subjected to chromatography on neutral alumina (300 g). Elution with hexane-benzene (1:1) and benzene-ethyl acetate (9.5: 0.5) gives an oil which on crystallization from a concentrated ether solution gives 1,7,12,12a-tetrahydrobenzo[1,2]cyclohepta[4,5,6-de]isoquinoline, m.p. 91° - 93° C, γmaxCHCl3 1629, 1588, 1578, 1490 cm-1. The corresponding hydrochloride acid addition salt has m.p. 285° - 289° C, after recrystallization from chloroform-ether and methanol-ether.

Workup

  1. customat 155° - 160° C.
  2. customThe darkish reaction mixture
  3. additionis poured hot
  4. stirringAfter stirring for 0.5 hr
  5. dissolutionthe precipitate is almost dissolved
  6. washThe combined chloroform solutions are washed with water
  7. dry with materialdried (Na2SO4)
  8. customto give a dark residue
  9. washElution with hexane-benzene (1:1) and benzene-ethyl acetate (9.5: 0.5)
  10. customgives an oil which
  11. customon crystallization from a concentrated ether solution

Sources & evidence

ORD record
ord-00837199758b40bfa0969683aa953e75
Source dataset
uspto-grants-1977_10
Patent number
US04054569

Reaction notes

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