1,1-Dichloroethane → HCID 69004095, compound

HRID 1435152Notes

Reaction equation

HRID 1435152 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH2:15])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].ClC(Cl)C.C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)Cl.CN(C)C=O>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][CH2:19][C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[Cl:16])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

8

Reactant 5

HCID 63651,1-DichloroethaneHCID 69962-ChlorobenzaldehydeHCID 11430Potassium CarbonateHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 69004095HCID 69004095, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a round bottom flask (50 mL) under nitrogen with stirring, is added N-Boc-4-(aminomethyl)-piperidine (0.500 g, 2.33 mmol), 2-chlorobenzaldehyde (0.275 mL, 0.344 g, 2.45 mmol) and sodium triacetoxyborohydride (1.483 g, 6.99 mmol) to dichloroethane (20 mL) and dimethylformamide (3 mL). Reaction is allowed to stir for 2 days. TLC (10% MeOH/DCM; starting material r.f 0.1, product r.f. 0.6). Reaction is then poured onto saturated potassium carbonate (c.a. 80 mL) and the product is extracted with ethyl acetate (c.a. 100 mL). This is dried over magnesium sulphate and concentrated in vacuo. The residue is taken up in methanol and placed on a 10 g SCX-2 column and washed with methanol. The product is eluted with 3.5M ammonia in methanol solution. The resultant solution is concentrated in vacuo to afford the N-Boc-4-(2-chlorobenzylaminomethyl)piperidine as a colourless oil (0.677 g, 86%).

Workup

  1. customReaction
  2. stirringto stir for 2 days
  3. customReaction
  4. extractionthe product is extracted with ethyl acetate (c.a. 100 mL)
  5. dry with materialThis is dried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. washwashed with methanol
  8. washThe product is eluted with 3.5M ammonia in methanol solution
  9. concentrationThe resultant solution is concentrated in vacuo

Sources & evidence

ORD record
ord-aadedbb8ab8444e78751c10160d2b5ff
Source dataset
uspto-grants-2009_11
Patent number
US07615648B2

Reaction notes

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