Ammonia → Phosphonium, (3-aminopropyl)triphenyl-, bromide, hydrobromide (1:1:1)

HRID 58325Notes

Reaction equation

HRID 58325 reaction equation
[Br-:1].[Br:2][CH2:3][CH2:4][CH2:5][P+:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH3:25].CO>>[BrH:2].[Br-:1].[NH2:25][CH2:3][CH2:4][CH2:5][P+:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 2723862(3-Bromopropyl)triphenylphosphonium bromide

Product 1

HCID 19897092Phosphonium, (3-aminopropyl)triphenyl-, bromide, hydrobromide (1:1:1)Yield 41%

Conditions

Temperature
85 °C

Procedure

(3-bromopropyl)(triphenyl)phosphonium bromide (4.9 g, 10.0 mmol) was treated with 7 M ammonia in methanol (97 mL, 680 mmol) in a sealed tube. The mixture was heated at 85° C. for 4 hours and cooled to room temperature. The volatiles were removed, and the resultant semi-solid was purified on a silica gel column eluting with first with 20% methanol in methylene chloride followed by 25% 1 M ammonia in methanol and methylene chloride to give the title compound (2.07 g) in a 41% yield.

Workup

  1. temperaturecooled to room temperature
  2. customThe volatiles were removed
  3. customthe resultant semi-solid was purified on a silica gel column
  4. washeluting with first with 20% methanol in methylene chloride

Sources & evidence

ORD record
ord-7663f93f67704d7db8a3f4d8f1aeefa8
Source dataset
uspto-grants-2016_09
Patent number
US09434753B2

Reaction notes

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