Ethylene → HCID 21702135, compound

HRID 1596606Notes

Reaction equation

HRID 1596606 reaction equation
C([N:4]([CH2:18]CC)[CH:5]1[CH2:17][CH2:16][C:8]2[C:9]3C=C[NH:12][C:13]=3[CH:14]=[CH:15][C:7]=2[CH2:6]1)CC.C1(=O)OC(=O)C2=C[CH:28]=[CH:29][CH:30]=C12.O=[S:33](Cl)Cl.C=C.[Al+3].[Cl-].[Cl-].[Cl-].C[CH:43]([NH2:50])[C:44]1C=CC=C[CH:45]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(Cl)(=O)CC>C(Cl)Cl.CCN(CC)CC.ClCCCl.CC(O)=O.C1C=CC=CC=1>[NH2:12][CH:13]1[CH2:14][CH2:15][C:7]2[C:8](=[CH:16][C:17]3[S:33][C:18]([N:50]([CH2:30][CH2:29][CH3:28])[CH2:43][CH2:44][CH3:45])=[N:4][C:5]=3[CH:6]=2)[CH2:9]1

Participants

14

Reactant 8

HCID 6325EthyleneHCID 6811Phthalic AnhydrideHCID 74081-PhenethylamineHCID 24386Thionyl ChlorideHCID 62324Propionyl chlorideHCID 5049666Sodium triacetoxyborohydrideHCID 6451240Aluminum(III) ChlorideHCID 13342884HCID 13342884, compound

Product 1

HCID 21702135HCID 21702135, compound

Reagents, catalysts & solvents 5

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent2×HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

* Synthesis is performed analogous to Hansson et al, Synthesis and Pharmacology od Dipropyl(6,7,8,9-tetrahydro-3H-benzo[e]indol-7-yl)-amine enantiomers, 9th Noordwijkerhout-Camerino Symposium, May 23-27, 1993, Noordwijkerhout, The Netherlands (poster presentation). Reagents: (a) Phthalic anhydride, HOAc, Δ; (b) SOCl2, CH2Cl2 Δ; (c) ethene, AlCl3, benzene, 0° C.; (d) α-methyl-benzylamine, NaB(OAc)3H, cat. HOAc, 1,2-dichloroethane; (e) propionyl-chloride, Et3N, CH2Cl2; (f) separation of diastereomers; (g) H2NNH2.H2O, EtOH, Δ; (h) LiAlH4, Et2O, r.t.; (i) KSCN, Br2, HOAc, r.t.; (j) separation of possible regioisomers; (k) HCO2NH4, Pd/C 10%, MeOH, Δ; (l) acyl chloride, Et3N, CH2Cl2; (m) BH3 in THF, Et2O, Δ.

Workup

  1. custom* Synthesis
  2. custom(f) separation of diastereomers
  3. custom(h) LiAlH4, Et2O, r.t.
  4. custom(i) KSCN, Br2, HOAc, r.t.
  5. custom(j) separation of possible regioisomers

Sources & evidence

ORD record
ord-130bab90cc384066a9ffe11ad554d8f2
Source dataset
uspto-grants-2001_09
Patent number
US06291494B1

Reaction notes

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