2-Naphthylacetonitrile → tert-Butyl 4-cyano-4-(naphthalen-2-yl)piperidine-1-carboxylate

HRID 1682993Notes

Reaction equation

HRID 1682993 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]#[N:13].Cl[CH2:15][CH2:16][N:17]([CH2:25][CH2:26]Cl)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>CS(C)=O>[C:21]([O:20][C:18]([N:17]1[CH2:25][CH2:26][C:11]([C:12]#[N:13])([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH2:15][CH2:16]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 820082-NaphthylacetonitrileHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

Product 1

HCID 49760261tert-Butyl 4-cyano-4-(naphthalen-2-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Combine naphth-2-ylacetonitrile (10 mmol) and 2-chloro-N-(2-chloroethyl)-N-tert-Butoxycarbonyl-ethanamine (11 mmol) in DMSO (30 mL). Add portionwise, NaNH2 (22 mmol). After the addition, stir for an additional 0.5 h. Pour the contents of the flask over ice (150 g). Extract the mixture with dichloromethane. Dry the organic phase over MgSO4, filter, and concentrate in vacuo to give a residue. Purify to give the title compound.

Workup

  1. additionAdd portionwise
  2. additionAfter the addition
  3. extractionExtract the mixture with dichloromethane
  4. dry with materialDry the organic phase over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customto give a residue
  8. customPurify

Sources & evidence

ORD record
ord-816283b3b575404ca398197f5fe61ef6
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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