Dimethylformamide → Tert-butyl 4-(1-(3-(cyclopropylmethoxy)-5-methoxybenzamido)ethyl)piperidine-1-carboxylate

HRID 881985

Reaction equation

HRID 881985 reaction equation
C1(CC[C:6]2[CH:7]=[C:8]([CH:12]=[C:13]([O:15][CH3:16])[CH:14]=2)[C:9]([OH:11])=O)CC1.[NH2:17][CH:18]([CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)[CH3:19].C(N(CC)CC)C.CN(C(ON1N=NC2C=C[CH:53]=[CH:54][C:49]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN([CH:65]=[O:66])C>O>[CH:53]1([CH2:16][O:15][C:13]2[CH:12]=[C:8]([CH:7]=[C:6]([O:66][CH3:65])[CH:14]=2)[C:9]([NH:17][CH:18]([CH:20]2[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH2:24][CH2:25]2)[CH3:19])=[O:11])[CH2:54][CH2:49]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22647295tert-Butyl 4-(1-aminoethyl)piperidine-1-carboxylateHCID 894637533-(2-Cyclopropylethyl)-5-methoxybenzoic acid

Product 1

HCID 89464457Tert-butyl 4-(1-(3-(cyclopropylmethoxy)-5-methoxybenzamido)ethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-(2-cyclopropylethyl)-5-methoxybenzoic acid (2.4 g, 10.7 mmol) and tert-butyl 4-(1-aminoethyl)piperidine-1-carboxylate (2.4 g, 10.7 mmol) in DMF (40 ml), was added triethyl amine (4.47 ml). After stirring for 10 minutes at room temperature TBTU (5.15 g, 16.1 mmol) was added in portions. The reaction mixture was stirred at room temperature for 2 hours. 100 ml H2O was added and the product was extracted into ethyla acetate. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by using normal phase chromatography eluting with petroleum ether containing 10% ethyl acetate to give tert-butyl 4-(1-(3-(cyclopropylmethoxy)-5-methoxybenzamido)ethyl)piperidine-1-carboxylate (3.0 g).

Workup

  1. additionwas added in portions
  2. extractionthe product was extracted into ethyla acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified
  7. washeluting with petroleum ether containing 10% ethyl acetate

Sources & evidence

ORD record
ord-f87213cc2a164907857dba4e43b554d0
Source dataset
uspto-grants-2015_03
Patent number
US08993757B2

Linked notes

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