Hydrochloric Acid → 4-methoxy-2-nitro-N-(1-phenylmethyl-4-piperidinyl)-benzylamine

HRID 2217276Notes

Reaction equation

HRID 2217276 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1.[C:14]1([CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[BH4-].[Na+].Cl>CO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:27][CH:24]2[CH2:25][CH2:26][N:21]([CH2:20][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:22][CH2:23]2)=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3576914-Methoxy-2-nitrobenzaldehydeHCID 4158521-Benzyl-4-piperidylamineHCID 4311764Sodium borohydride

Product 1

HCID 179586954-methoxy-2-nitro-N-(1-phenylmethyl-4-piperidinyl)-benzylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.0 g (16.561 mmol) of 4-methoxy-2-nitrobenzaldehyde, 3.2 g (16.817 mmol) of 1-phenylmethyl-4-piperidinamine and 30 mL of methanol was stirred for 2 hours at ambient temperature. Then 681 mg (18.0 mmol) of sodium borohydride was added and stirring was continued for one hour at ambient temperature. The mixture was stirred into 500 mL of ice water and carefully acidified with 10% hydrochloric acid. The solution obtained was washed twice with 50 mL of tert-butylmethylether, then made alkaline with 20% sodium hydroxide solution and extracted exhaustively with tert-butylmethylether. The final extracts obtained were combined, washed twice with 20 mL of water, dried over magnesium sulfate and evaporated down in vacuo. The colorless oil remaining was used in the next step without any further purification. Yield: 3.2 g (54% of theoretical). IR (KBr): no C═O; MS: M+=355.

Workup

  1. stirringstirring
  2. waitwas continued for one hour at ambient temperature
  3. customThe solution obtained
  4. washwas washed twice with 50 mL of tert-butylmethylether
  5. extractionextracted exhaustively with tert-butylmethylether
  6. customThe final extracts obtained
  7. washwashed twice with 20 mL of water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated down in vacuo
  10. customThe colorless oil remaining was used in the next step without any further purification

Sources & evidence

ORD record
ord-e4b1f3140591422fbfcecbaa7cd3a55b
Source dataset
uspto-grants-2008_08
Patent number
US07407963B2

Reaction notes

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