Toluene → 4-(8-Azaspiro[4.5]decan-8-yl)naphthalene-1-carbonitrile

HRID 916344Notes

Reaction equation

HRID 916344 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]#[N:13])=[CH:4][CH:3]=1.[CH:14](N(CC)C(C)C)(C)[CH3:15].[C:23]1([CH3:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[CH2:27]1[C:26]2([CH2:25][CH2:24][N:1]([C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]([C:12]#[N:13])=[CH:4][CH:3]=3)[CH2:15][CH2:14]2)[CH2:29][CH2:23][CH2:28]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 428284-Amino-1-naphthalenecarbonitrileHCID 81531Diisopropylethylamine

Product 1

HCID 692239744-(8-Azaspiro[4.5]decan-8-yl)naphthalene-1-carbonitrileYield 5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Amino-1-naphthalenecarbonitrile (168.20 mg), 3,3-tetramethylene-1,5-dibromopentane (284 mg, 1.0 mmol, Klitgaard, N. et al., Acta Chem. Scand. 1970, 24, 33-42), N,N-diisopropylethylamine (323 mg, 2.5 mmol) and toluene (15 mL) were heated to 120° C. for 16 h. The crude product was poured in water (100 mL), extracted with ethyl acetate (3×100 mL), the combined organic layers dried over sodium sulfate, filtered and concentrated in vacuo. Purification by preparative TLC (dichloromethane, 3× eluted) afforded the title compound (14 mg, 5.0%) as an off-white solid.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. dry with materialthe combined organic layers dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification
  6. washby preparative TLC (dichloromethane, 3× eluted)

Sources & evidence

ORD record
ord-7936259c19c3475f8b9f6014b3f36208
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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