Diisopropylethylamine → (7-Ethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-(1-methanesulfonyl-piperidin-4-ylmethyl)-propyl-amine

HRID 1168884Notes

Reaction equation

HRID 1168884 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]([NH:14][CH2:15][CH2:16][CH3:17])[CH2:11]2)=[CH:6][CH:5]=1)[CH3:2].[CH3:18][S:19]([N:22]1[CH2:27][CH2:26][CH:25]([CH:28]=O)[CH2:24][CH2:23]1)(=[O:21])=[O:20].CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]([N:14]([CH2:28][CH:25]3[CH2:26][CH2:27][N:22]([S:19]([CH3:18])(=[O:21])=[O:20])[CH2:23][CH2:24]3)[CH2:15][CH2:16][CH3:17])[CH2:11]2)=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 109543721-(Methylsulfonyl)piperidine-4-carbaldehydeHCID 22560667(7-Ethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine

Product 1

HCID 21362794(7-Ethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-(1-methanesulfonyl-piperidin-4-ylmethyl)-propyl-amine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of afford (7-ethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine (200 μL of a 0.25M solution in 1,2-dichloroethane, 50 μmole) was added 220 μL of a solution of 1-(methylsulfonyl)-4-piperidinecarboxaldehyde (0.25 M in 1,2-dichloroethane) followed by 30 μL DIEA and 300 μL of a 0.25 M slurry of sodium triacetoxyborohydride in 1,2-dichloroethane. The solution was shaken at 25° C. for 48 h under N2. The reaction was quenched with 1 mL 2% NaOH and the mixture was transferred along with 0.5 mL H2O and EtOAc to workup flasks. The flask was shaken, allowed to settle and the aqueous phase was removed and discarded. The organic phase was washed with water, transferred into a tube and concentrated in vacuo. The final product was isolated by preparative RPHPLC (YMC Combiprep ODS-A column, 10-90% acetonitrile: water (0.1% TFA)) to afford (7-ethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-(1-methanesulfonyl-piperidin-4-ylmethyl)-propyl-amine (8 mg) 104[M+H]+=409.

Workup

  1. customThe reaction was quenched with 1 mL 2% NaOH
  2. stirringThe flask was shaken
  3. customthe aqueous phase was removed
  4. washThe organic phase was washed with water
  5. customtransferred into a tube
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32aad7c8fb554e00833916efb31df37b
Source dataset
uspto-grants-2003_09
Patent number
US06627644B2

Reaction notes

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