Dimethylamine → HCID 86720918, compound

HRID 524860Notes

Reaction equation

HRID 524860 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1.[CH3:17][N:18](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:19].[B-](F)(F)(F)F.CNC>CO>[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH2:9][CH2:10][CH:11]([C:14]([N:18]([CH3:19])[CH3:17])=[O:16])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86720916HCID 86720916, compound

Product 1

HCID 86720918HCID 86720918, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
120 °C

Procedure

A microwave vial was charged with 1-(3-amino-4-pyridyl)piperidine-4-carboxylic acid (125 mg, 0.197 mmol), TBTU (200 mg, 0.62 mmol) and N-methylmethanamine (3.5 mL, 2M in MeOH). The tube was sealed and the mixture stirred for 3 h at 120° C. The crude was redissolved in MeOH and loaded into a MeOH pre-washed SCX column, rinsed with MeOH and the product was released with methanolic ammonia. The ammonia extracts were concentrated under reduced pressure to yield 1-(3-aminopyridin-4-yl)-N,N-dimethylpiperidine-4-carboxamide. MS (ES+) 249.2.

Workup

  1. customThe tube was sealed
  2. washrinsed with MeOH
  3. concentrationThe ammonia extracts were concentrated under reduced pressure

Sources & evidence

ORD record
ord-87e18eb5943e49508e16b96fc8a51255
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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