4-(Aminomethyl)piperidine → (R)-alpha-Amino-N-methyl-N-[(2'-nitro)[1,1'-biphenyl]-4-yl]-benzenebutanamide

HRID 1923Notes

Reaction equation

HRID 1923 reaction equation
C1C2C(COC([NH:18][C@H:19]([CH2:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:20]([N:22]([CH3:38])[C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[N+:35]([O-:37])=[O:36])=[CH:25][CH:24]=3)=[O:21])=O)C3C(=CC=CC=3)C=2C=CC=1.NCC1CCNCC1>C(Cl)Cl>[NH2:18][C@H:19]([CH2:39][CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:20]([N:22]([CH3:38])[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[N+:35]([O-:37])=[O:36])=[CH:25][CH:24]=1)=[O:21]

Participants

4

Reactant 2

HCID 235274-(Aminomethyl)piperidineHCID 22883387(R)-alpha-[N-(9-Fluorenylmethoxycarbonyl)amino]-N-methyl-N-[(2'-nitro)[1,1'-biphenyl]-4-yl]-benzenebutanamide

Product 1

HCID 22883384(R)-alpha-Amino-N-methyl-N-[(2'-nitro)[1,1'-biphenyl]-4-yl]-benzenebutanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The FMOC amide from Step F (1.15 g; 1.88 mmol) was dissolved in methylene chloride (10 ml) and 4-(aminomethyl)piperidine (1 ml) added. The reaction mixture was stirred at room temperature. The reaction mixture was stirred for 15 minutes and then quenched by adding water. The methylene chloride phase was separated, dried over ahnydrous potassium carbonate powder, filtered and evaprated under reduced pressure to afford an orange-yellow oil. The oil was chromatographed on silica gel using an eluant of ethyl acetate and methanol (9:1 v/v). A pale yellow oil (517 mg; 70.6%) was isolated of the amine. FAB-MS:- calculated for C23H23N3 O3 389.2 found 389.9 (M).

Workup

  1. stirringThe reaction mixture was stirred for 15 minutes
  2. customquenched
  3. additionby adding water
  4. customThe methylene chloride phase was separated
  5. dry with materialdried over ahnydrous potassium carbonate powder
  6. filtrationfiltered
  7. customto afford an orange-yellow oil
  8. customThe oil was chromatographed on silica gel using an eluant of ethyl acetate and methanol (9:1 v/v)

Sources & evidence

ORD record
ord-4973b5510ea745408780d7b531a293b6
Source dataset
uspto-grants-1998_03
Patent number
US05726319

Reaction notes

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