Sodium Iodide → (6-dibenzylamino-1H-indol-3-yl)-acetonitrile

HRID 37943Notes

Reaction equation

HRID 37943 reaction equation
C(OC(C1[C:12]2[NH:13][C:14]3[CH:15]=[C:16]([N:20]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:17]=[CH:18][C:19]=3[C:11]=2[C:10](C)(C)[CH2:9][NH:8]C=1)=O)C.C(Br)C1C=CC=CC=1.NC1C=C2C(C(CC#N)=CN2)=CC=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O.CN(C=O)C>[CH2:28]([N:20]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:15]=[C:14]2[C:19]([C:11]([CH2:10][C:9]#[N:8])=[CH:12][NH:13]2)=[CH:18][CH:17]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 513582822-(6-Amino-1h-indol-3-yl)acetonitrileHCID 66640357Azepino[4,5-b]indole-5-carboxylic acid, 8-[bis(phenylmethyl)amino]-1,2,3,6-tetrahydro-1,1-dimethyl-, ethyl ester

Product 1

HCID 66641045(6-dibenzylamino-1H-indol-3-yl)-acetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To prepare 8-dibenzylamino-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester: Benzyl bromide (10 mL, 84.2 mmol) was added to a stirred mixture of (6-amino-1H-indol-3-yl)acetonitrile (Brown, R. K.; Garrison, R. A., J. Am. Chem. Soc. (1955), Vol. 77, pp. 3839-3842) (5.16 g, 30.14 mmol), potassium carbonate (10.83 g, 78.36 mmol), sodium iodide (560 mg, 3.74 mmol) and anhydrous DMF (150 mL) at ambient temperature under nitrogen. The resulting mixture was stirred at ambient temperature overnight, then poured into a mixture of water, and extracted with ethyl acetate. The combined extracts were washed with ammonium chloride solution, and evaporated in vacuo. The residue was purified by chromatography on silica gel eluting with hexane-ethyl acetate (85:15) to give (6-dibenzylamino-1H-indol-3-yl)-acetonitrile (8.8 g); MS (ES): 352 (MH+), which was then treated in a manner similar to that described in Example 34C-G but replacing (6-benzyloxy-1H-indol-3-yl)acetonitrile with (6-dibenzylamino-1H-indo-3-yl)acetonitrile at Step C.

Workup

  1. customat ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with ammonium chloride solution
  4. customevaporated in vacuo
  5. customThe residue was purified by chromatography on silica gel eluting with hexane-ethyl acetate (85:15)

Sources & evidence

ORD record
ord-c81006c5b7dc42c3978594db2fec3d48
Source dataset
uspto-grants-2013_09
Patent number
US08524704B2

Reaction notes

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