Dichloromethane → 1-[4-(Benzoxazol-2-yl)benzyloxy]-3-(4-phenylbutoxy)-2-propanamine hydrochloride

HRID 863853Notes

Reaction equation

HRID 863853 reaction equation
C([NH:20][CH:21]([CH2:40][O:41][CH2:42][CH2:43][CH2:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[O:32][C:33]3[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=3[N:35]=2)=[CH:27][CH:26]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(Cl)[Cl:53]>CO>[ClH:53].[O:32]1[C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[N:35]=[C:31]1[C:28]1[CH:29]=[CH:30][C:25]([CH2:24][O:23][CH2:22][CH:21]([NH2:20])[CH2:40][O:41][CH2:42][CH2:43][CH2:44][CH2:45][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 19420792N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-(4-phenylbutoxy)-2-propanamine

Product 1

HCID 194207361-[4-(Benzoxazol-2-yl)benzyloxy]-3-(4-phenylbutoxy)-2-propanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent4×

Procedure

N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-(4-phenylbutoxy)-2-propanamine (0.3 g; 0.45 mmol) is dissolved in CH2Cl2 (3 ml) and MeOH (3 ml) and acidified to pH3 with acidic methanol. The reaction is stirred 1.5 hours, concentrated and purified by column chromatography with 8% MeOH/CH2Cl2. The product is isolated, dissolved in MeOH and acidified with acidic methanol. The solution is concentrated to yield 1-[4-(benzoxazol-2-yl)benzyloxy]-3-(4-phenylbutoxy)-2-propanamine hydrochloride (m.p. 125°-126° C. ).

Workup

  1. concentrationconcentrated
  2. custompurified by column chromatography with 8% MeOH/CH2Cl2
  3. customThe product is isolated
  4. concentrationThe solution is concentrated

Sources & evidence

ORD record
ord-fee7da58c65246fd9d561e80a7d3ea42
Source dataset
uspto-grants-1996_10
Patent number
US05561143

Reaction notes

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