Acetic Acid → Ammonia methanol dichloromethane

HRID 33698Notes

Reaction equation

HRID 33698 reaction equation
Cl.[N:2]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:49][CH:50]([Cl:52])C>>[NH3:2].[CH3:9][OH:10].[Cl:49][CH2:50][Cl:52].[CH2:23]([N:20]1[CH2:19][CH2:18][N:17]([C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:2]3[CH2:6][CH2:5][CH2:4][CH2:3]3)=[CH:16][CH:15]=2)[CH2:22][CH2:21]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 99018441-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-piperazine hydrochloride

Product 2

HCID 99699911-Benzyl-4-[4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-piperazineHCID 21584172Ammonia methanol dichloromethaneYield 5%

Procedure

A solution of the product of Example 23 (148 mg), benzaldehyde (520 mg), and acetic acid (25 mg) in dichloroethane (3 mL) was treated with sodium triacetoxyborohydride (121 mg). After 14 h, the reaction was quenched with saturated aqueous sodium bicarbonate, and the aqueous phase was extracted with dichloromethane (120 mL). The organic phase was dried (magnesium sulfate) and evaporated in vacuo. Silica gel chromatography of the residue (5% 2M ammonia-methanol/dichloromethane) gave the title compound as a light yellow solid (8 mg). 1H NMR (400 MHz, CDCl3): 7.36-7.24 (m, 5H), 6.94-6.81 (m, 4H), 3.96 (t, J=6.4 Hz, 2H), 3.56 (s, 2H), 3.08 (t, J=4.9 Hz, 4H), 2.64-2.60 (m, 4H), 2.04-1.94 (m, 2H), 1.80-1.75 (m, 4H).

Workup

  1. customthe reaction was quenched with saturated aqueous sodium bicarbonate
  2. extractionthe aqueous phase was extracted with dichloromethane (120 mL)
  3. dry with materialThe organic phase was dried (magnesium sulfate)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-accdf9f94e824b48ab1a2eac8bb2b6b7
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Reaction notes

Loading…